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73-31-4 Usage

Description

Melatonin, at times referred to as the “hormone of darkness,” normally is secreted during the night. It is synthesized in the pineal gland, and its secretion is controlled by the suprachiasmatic nucleus, following an endogenous circadian rhythm. Studies indicate that melatonin may

Uses

Melatonin has complex effects on apoptotic pathways, inhibiting apoptosis in immune cells and neurons but enhancing apoptotic cell death of cancer cells. Inhibits proliferation/metastasis of breast cancer cells by inhibiting estrogen receptor action.

Mechanism of action

Melatonin is a naturally occurring hormone produced by the pineal gland and is structurally related to serotonin. Physiologically, melatonin secretion increases soon after the onset of darkness, peaks at 2-4 am and diminishes during the second half of the night. Melatonin is associated with the control of circadian rhythms and entrainment to the light-dark cycle. It is also associated with a hypnotic effect and increased propensity for sleep. The activity of melatonin at the MT1 MT2 receptors is believed to contribute to its sleep-promoting properties via their distinct actions on the circadian clock. The MT1 receptors are thought to inhibit neuronal firing, while the MT2 receptors have been implicated in the phase-shifting response.

Definition

ChEBI: A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen atom is replaced by a 2-(5-methoxy-1H-indol-3-yl)ethyl group. It is a hormone secreted by the pineal gland in humans.

Uses

Immunostimulant;Melatonin receptor ligand

Uses

Hormone postulated to mediate photoperiodicity in mammals. Inhibits cerebellar nitric oxide synthetase

Clinical Use

Melatonin is most effective in young individuals and appears to be less effective in elderly individuals (possibly because of a decreased number of receptors). Melatonin causes a phase shift of approximately 1 hour per day. This means that the use of melatonin in the morning can delay the onset of evening sleepiness, whereas melatonin taken in the evening has been associated with faster onset of sleep and increased total sleep time. Melatonin is sold as a food supplement in the United States, but it has become popular for use as a hypnotic and for alleviating jet lag (a flight across five or more time zones) and helping to resynchronize individuals who have difficulty adapting to night-shift work. have effects on circadian rhythm and sleep processes. The presence of a pharmacologically specific receptor for melatonin in which the molecular structure is known are referred to as MT1, MT2, and MT3 receptors. The MT1 and MT2 receptors are high-affinity G protein coupled receptors, whereas MT3 is a form of quinone reductase. The MT1 receptor appears to be primarily involved in initiating sleep, whereas the MT2 receptor appears to mediate melatonins effect in the eye, circadian rhythm, and vascular effects. The importance of MT3, although widely distributed in different tissues, is currently unknown. The normal physiological concentration of melatonin observed at night is approximately 100 to 200 pg/mL, and oral doses of 0.1 to 0.3 mg of melatonin are adequate to obtain these concentrations even though melatonin frequently is given at doses of 1 to 10 mg to obtain supraphysiological levels. These higher doses may be the reason for some of the side effects not currently associated with the melatonin receptors.

Physiological functions

1. The effect to brain: the melatonin obtained by brain mainly gathers in midbrain and hypothalamus and it adds the activity of brain pyridoxal kinase, thus promoting glutamic acid decarboxylation to γ-amino butyric acid, 5-hydroxytryptophane decarboxylation to 5-hydroxytryptamine, both of which can inhibit the increase of the neurotransmitter content and have an effect of adjustment and mitigation on central nervous system. 2. The effect to hypothalamus and pituitary: materials like polypeptide produced by pineal body still have thyrotropin-releasing hormone(TRH) and luteinizing hormone releasing hormone(LRH) which are same with what hypothalamus produces except AVT. After injection of melatonin, gonadotropin (GnH)(FSH,LH) and melanocyte stimulating hormone(MSH) are lowered while growth hormone increases. Cutting pineal gland will cause pituitary hypertrophy, increase pituitary secretion and lower prolactin(PRL) and antidiuretic hormone (ADH). 3. The relation to gonad: melatonin has an inhibitory effect on the reproductive system. Clinically, main cytoma of pineal body can lead to pubertal delay and when teratoma appears in pineal body, it may result in sexual precocity because main cells are excluded. Ambient light and sympathetic nerve can affect the function of the reproductive system by inhibiting the synthesis and release of melatonin in pineal gland. 4. The relation to thyroid: by injecting melatonin, thyroid secretion will decrease. This may be caused through the inhibition of the hypothalamus release and Thyroid Stimulating Hormone (TSH) secretion of pituitary, hence holding back the function of thyroid. 5. The relation to adrenal cortex: melatonin has a strong inhibitory effect on adrenal cortex. If we inject pineal body extracts to healthy people, we will find that their aldosterone secretion and 17-ketosteroid output will decrease. 6. The relation to pancreatic island: melatonin can lower blood glucose and increase sugar tolerance. In conclusion, pineal gland can assist pituitary to jointly adjust endocrine function and play an vital role in keeping relatively constant in body environment and controlling some endocrine function, especially for gonad.

Chemical Properties

Off-White Powder

Uses

1. Melatonin can be used as medicine health care products, so as to enhance people’s immune function, preventing aging and back to youth. What’s more, it is also a kind of natural “sleeping pill”. 2. Melatonin is a kind of hormone secreted by pineal body of pituitary gland in the body. The amount of melatonin has something to do with light. The weaker the light is, the more the melatonin is, whereas the less. In addition, it is helpful to one’s sleep. 3. Biochemical research.

Biological Activity

Endogenous hormone that acts as an agonist at melatonin receptors MT 1 and MT 2 . Exhibits a prominent role in the control of circadian rhythm, displays immunomodulatory activity and acts as a powerful antioxidant in vivo .

Occurrence

Melatonin is a naturally occurring hormone in the body.

Biological Activity

Melatonin is a naturally compound found in animals, plants, and microbes. It is a hormone secreted by the pineal gland. Melatonin can directly neutralize a number of ROS, stimulate several antioxidant enzymes, reduce UV-induced erythema, modulate the expression of apoptosis and alleviate sleep disturbances. The mechanism of biological effects is via activation of melatonin receptors or protection of nuclear and mitochondrial DNA. In the skin, melatonin scavenges and inactivates free radicals arising from UV irradiation. Melatonin represents a substance which protects cells from UVA and UVB action in vitro and in vivo experiments. Preincubation with melatonin can lead to the normalization of the decreased UV-induced mitochondrial membrane potential. Such effects are followed by suppression of the activation of mitochondrial pathway-related initiator caspase 9 (casp-9), but not of death receptor-dependent casp-8. Melatonin also down-regulates casp-3/casp-7 and reduces PARP activation (Fischer et al,. 2008).

Chemical properties

Melatonin is a slightly off-white, odourless crystalline powder. It is very slightly soluble in water and in dilute hydrochloric acid. Melatonin is a small molecule, a derivative of the amino acid tryptophan, N-acetyl-5 methoxytryptamine. It is a potent hormone with well-recognized activities and the potential to influence many bodily functions. It is produced by the pineal gland in the brain and is secreted when the body recognizes darkness. Melatonin has intense effects on the timing of the sleep/awake cycle, regulating the circadian rhythms of several biological functions. This is its most studied biological activity. Melatonin, as a multifunctional hormone, appears to regulate or modulate other functions in humans through the activation of its receptors and works as a strong antioxidant that protects the DNA. Melatonin’s antioxidant activity may reduce Parkinson’s disease development, prevent cardiac arrhythmia, and, in animals, promote longevity.

Synthesis of Melatonin

Pineal cells obtain tryptophan from blood circulation and become 5-hydroxytryptophane catalyzed by hydroxylase and 5-hydroxytryptophane turns into 5-hydroxytryptamine after decarboxylated by decarboxylase. There are three possible changes for 5-hydroxytryptamine: for the first part it may turn into 5-hydroxyl-benzpyrole acetic acid when deaminated by monoamine oxidase; for another part, some 5-hydroxytryptamine will leave the pineal cell and be taken in by sympathetic nerve ending and stored with neurotransmitter and noradrenalin; for the remaining part, the 5-hydroxytryptamine will be acetylated by N-acetyl-5-hydroxy tryptamine transferase and then be o-methoxy by hydroxylation indole-o-methyl converzyme, finally forming melatonin. After being synthesized, melatonin will be released by cells and enter into blood circulation through cerebrospinal fluid or directly, where noradrenalin may strengthen the synthesis, the speed of which depends on activity of hydroxylase in liver microsomes. Catalyzed by the hydroxylase, 6-hydroxylmelatonin is formed, soon afterwards it combines with glucuronic acid and sulfate, excreting through urine.

description

Melatonin is a hormone secreted by the pineal gland, and its chemical structure was 5-methoxy-N-acetyl tryptamine, the physiological function of inhibiting gonad, thyroid, adrenal gland, parathyroid gland and pituitary function, inhibit precocious puberty, reduce pituitary Melanotropin secretion; and has a central nervous system function, can improve the convulsion the threshold, cause drowsiness. When pinealectomy after the animal experiment showed hyperplasia of the glands, weight increase, especially sex and sexual organs of immature rats early, pituitary secretion of LH and FSH increased, increasing secretion of thyroid and adrenal cortex hormone melatonin. More reduced pituitary MSH and whiten the skin of this role. Effects on the central nervous system, in the human EEG showed slow rhythm, increased seizure threshold, sleepiness, but does not affect their behavior and personality, of temporal lobe epilepsy and Ba Jinsen disease can reduce the motor nerve Abnormal EEG changes.

Veterinary Drugs and Treatments

Melatonin may be useful to treat Alopecia-X in Nordic breeds, canine pattern baldness, or canine recurrent flank alopecia in dogs. It has been used anecdotally for the treatment of sleep cycle disorders in cats and geriatric dogs and to treat phobias and separation anxiety in dogs. Melatonin implants are used in the mink and fox pelt industries to promote the development of luxurious hair coats. Implants are also used to improve early breeding and ovulation rates in sheep and goats. Preliminary research is being done for this purpose in horses also. In pigs, one study (Bubenik, Ayles et al. 1998) demonstrated that 5 mg/kg in feed reduced the incidence of gastric ulcers in young pigs.

Uses

Melatonine can be used in sleep induction, modifies circadian rhythm, antioxidant, free radical scavenger

World Health Organization (WHO)

Melatonin is promoted as a cure for travel sickness, jet-lag and insomnia and has recently been claimed in the United States to reverse the ageing process. A synthetic version has been freely available from health food shops and pharmacies as a "nutritional supplement" since 1993.
InChI:InChI=1/C13H16N2O2/c1-9(16)14-6-5-10-8-15-13-4-3-11(17-2)7-12(10)13/h3-4,7-8,15H,5-6H2,1-2H3,(H,14,16)

73-31-4 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (M1105)  Melatonin  >98.0%(HPLC)(N) 73-31-4 1g 238.00CNY Detail
TCI America (M1105)  Melatonin  >98.0%(HPLC)(N) 73-31-4 5g 830.00CNY Detail

73-31-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name melatonin

1.2 Other means of identification

Product number -
Other names Acetamide, N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:73-31-4 SDS

73-31-4Synthetic route

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

acetic anhydride
108-24-7

acetic anhydride

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With pyridine In dichloromethane100%
In 1,2-dichloro-ethane at 0℃; for 1h;96%
With triethylamine95%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

acetyl chloride
75-36-5

acetyl chloride

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In dichloromethane at 25 - 30℃; Temperature;98.3%
With triethylamine In dichloromethane at 20℃;
With triethylamine In dichloromethane at 0 - 20℃; for 5h;
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

potassium thioacetate
10387-40-3

potassium thioacetate

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With tetrabutylammonium tetrafluoroborate In ethyl acetate at 20℃; Electrochemical reaction;97%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one
2735-73-1

1,3-diacetyl-1,3-dihydro-benzoimidazol-2-one

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.3h;93%
N-[2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethyl]acetamide

N-[2-(1-benzyl-5-methoxy-1H-indol-3-yl)ethyl]acetamide

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With ammonia; sodium In tetrahydrofuran at -78 - -33℃; for 1h;92%
vinyl acetate
108-05-4

vinyl acetate

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With agarose immobilized acetyltransferase from Mycobacterium smegmatis (MsAcT) In aq. phosphate buffer; dimethyl sulfoxide at 25℃; under 760.051 Torr; for 0.0833333h; pH=8.0; Flow reactor; Enzymatic reaction;92%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

thioacetic acid
507-09-5

thioacetic acid

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate In acetonitrile at 20℃; for 5h; Irradiation;92%
N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide
1020701-51-2

N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With tetraethylammonium perchlorate; triethylamine In dimethyl sulfoxide at 20℃; for 10h; Electrolysis; Green chemistry;92%
With 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In water; acetonitrile for 20h; Irradiation;81%
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

acetic anhydride
108-24-7

acetic anhydride

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 25℃; for 3h;90%
boron trifluoride methanol complex
16045-88-8, 373-57-9

boron trifluoride methanol complex

Nb-acetyl-1-hydroxytriptamine
136788-90-4

Nb-acetyl-1-hydroxytriptamine

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In methanol Heating;80%
methanol
67-56-1

methanol

Nb-acetyl-1-hydroxytriptamine
136788-90-4

Nb-acetyl-1-hydroxytriptamine

A

bufotenin
487-93-4

bufotenin

B

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With sulfuric acid Heating;A 7%
B 80%
methanol
67-56-1

methanol

Nb-acetyl-1-hydroxytriptamine
136788-90-4

Nb-acetyl-1-hydroxytriptamine

A

N-Acetyltryptamine
1016-47-3

N-Acetyltryptamine

B

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With boron trifluoride for 0.666667h; Product distribution; Further Variations:; Reagents; Temperatures; reaction times; Elimination; methoxylation; Heating;A 5%
B 80%
5-methoxylindole
1006-94-6

5-methoxylindole

2-acetylaminoethanol
142-26-7

2-acetylaminoethanol

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With dichloro(pentamethylcyclopentadienyl) iridium; caesium carbonate at 150℃; for 48h; Inert atmosphere; Sealed tube;78%
N-[(methyl)carbonyl]-2-pyrroline
23105-58-0

N-[(methyl)carbonyl]-2-pyrroline

4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In ethanol; water; acetic acid for 0.333333h; Cyclization; Fischer synthesis; Heating;75%
N-[2-(1-methanesulfonyl-5-methoxy-2,3-dihydro-1H-indol-3-yl)-ethyl]-acetamide
474640-48-7

N-[2-(1-methanesulfonyl-5-methoxy-2,3-dihydro-1H-indol-3-yl)-ethyl]-acetamide

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With sulfuric acid at 0℃; for 0.5h;72%
2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

ethyl acetate
141-78-6

ethyl acetate

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With acetic acid at 80℃; for 20h; Sealed tube;70%
With agarose immobilized acetyltransferase from Mycobacterium smegmatis (MsAcT) In aq. phosphate buffer; dimethyl sulfoxide at 25℃; under 760.051 Torr; for 0.0833333h; pH=8.0; Flow reactor; Enzymatic reaction;
N-acetyl-5-hydroxytryptamine
1210-83-9

N-acetyl-5-hydroxytryptamine

dimethyl sulfate
77-78-1

dimethyl sulfate

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With sodium hydroxide In water at 26℃; for 2.25h;61.4%
2-(2,4-dinitrophenylsulfenyl)melatonin
28772-49-8

2-(2,4-dinitrophenylsulfenyl)melatonin

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With nickel In 1,4-dioxane; water at 80 - 90℃; for 20h; until it lost its coloration;54%
N-allylacetamide
692-33-1

N-allylacetamide

carbon monoxide
201230-82-2

carbon monoxide

4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
Stage #1: N-allylacetamide; carbon monoxide With hydrogen; acetylacetonatodicarbonylrhodium(l); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In water; toluene at 70℃; under 7500.75 Torr; for 30h; Hydroformylation;
Stage #2: 4-methoxyphenylhydrazine hydrochloride Condensation;
Stage #3: With acetic acid for 0.166667h; Cyclization; Fischer indole reaction; Heating; Further stages.;
44%
4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

1-acetyl-2-methoxypyrrolidine
63050-21-5

1-acetyl-2-methoxypyrrolidine

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
In water; acetic acid Heating;32%
indole
120-72-9

indole

Nb-acetyl-1-methoxytryptamine
180910-62-7

Nb-acetyl-1-methoxytryptamine

A

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

B

N-[2-(5-methoxy-1'H-[1,3']biindolyl-3-yl)-ethyl]-acetamide

N-[2-(5-methoxy-1'H-[1,3']biindolyl-3-yl)-ethyl]-acetamide

C

N-[2-(5'-methoxy-1H,1'H-[3,4']biindolyl-3'-yl)-ethyl]-acetamide

N-[2-(5'-methoxy-1H,1'H-[3,4']biindolyl-3'-yl)-ethyl]-acetamide

D

N-[2-(5'-methoxy-1H,1'H-[3,7']biindolyl-3'-yl)-ethyl]-acetamide

N-[2-(5'-methoxy-1H,1'H-[3,7']biindolyl-3'-yl)-ethyl]-acetamide

Conditions
ConditionsYield
With methanesulfonyl chloride; triethylamine In chloroform Further byproducts given;A 7%
B 7%
C 12%
D 7%
5-methoxyindole-3-acetonitrile
2436-17-1

5-methoxyindole-3-acetonitrile

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With ethanol; sodium Erwaermen des Reaktionsprodukts mit Essigsaeure und Acetanhydrid auf 100grad;
Nb,Nb-diacetyl-5-methoxytryptamine
188396-98-7

Nb,Nb-diacetyl-5-methoxytryptamine

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With ammonium hydroxide In methanol Yield given;
(E)-3-(2-nitroethenyl)-5-methoxyindole
61675-19-2

(E)-3-(2-nitroethenyl)-5-methoxyindole

acetic anhydride
108-24-7

acetic anhydride

A

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

B

(E)-N-[2-(5-methoxy-1H-indol-3-yl)etenyl]acetamide

(E)-N-[2-(5-methoxy-1H-indol-3-yl)etenyl]acetamide

C

N-[(E)-2-(1-Acetyl-5-methoxy-1H-indol-3-yl)-vinyl]-acetamide

N-[(E)-2-(1-Acetyl-5-methoxy-1H-indol-3-yl)-vinyl]-acetamide

Conditions
ConditionsYield
With hydrogen; nickel In tetrahydrofuran under 3040 Torr; for 10h; Ambient temperature;
With sodium hydroxide; hydrogen; nickel 1.) THF, RT, 4 atm, 10 h, 2.) MeOH, RT, 4h; Yield given;
4-aminobutyraldehyde dimethyl acetal
19060-15-2

4-aminobutyraldehyde dimethyl acetal

4-methoxyphenylhydrazine hydrochloride
19501-58-7

4-methoxyphenylhydrazine hydrochloride

acetic anhydride
108-24-7

acetic anhydride

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
1.) 5 - 10 deg C, 1 h, 2.) AcOH, EtOH, H2O, 40 deg C, 12 h; Yield given; Multistep reaction;
5-methoxytryptamine hydrochloride
66-83-1

5-methoxytryptamine hydrochloride

[14C]acetyl-CoA

[14C]acetyl-CoA

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With sheep pineal supernatant (serotonin-N-acetyl transferase); Pargyline In phosphate buffer at 37℃; for 0.166667h; pH=6.8; Enzyme kinetics;
acetic anhydride
108-24-7

acetic anhydride

3-(2-isocyanato-ethyl)-5-methoxy-1H-indole

3-(2-isocyanato-ethyl)-5-methoxy-1H-indole

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
Stage #1: acetic anhydride; 3-(2-isocyanato-ethyl)-5-methoxy-1H-indole In acetic acid Heating;
Stage #2: With potassium carbonate In methanol at 20℃; Further stages.;
acetic anhydride
108-24-7

acetic anhydride

3-(2-isocyanato-ethyl)-5-methoxy-1H-indole

3-(2-isocyanato-ethyl)-5-methoxy-1H-indole

A

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

B

N-(2-(1-acetyl-5-methoxy-1H-indol-3-yl)ethyl)acetamide

N-(2-(1-acetyl-5-methoxy-1H-indol-3-yl)ethyl)acetamide

Conditions
ConditionsYield
In acetic acid Heating; Title compound not separated from byproducts.;
N-[2-(5-methoxy-1-nitroso-1H-indol-3-yl)ethyl]acetamide

N-[2-(5-methoxy-1-nitroso-1H-indol-3-yl)ethyl]acetamide

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Conditions
ConditionsYield
With Tris-HCl buffer In ethanol; water at 37℃; pH=7.40; Kinetics; Further Variations:; pH-values; Reagents; Solvents;
With Tris-HCl buffer; L-Cysteine In ethanol; water at 37℃; pH=7.40; Kinetics; Further Variations:; pH-values; Reagents;
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

N-(2-(5-methoxy-1H-indol-3-yl-2,4,6-d3)ethyl)acetamide

N-(2-(5-methoxy-1H-indol-3-yl-2,4,6-d3)ethyl)acetamide

Conditions
ConditionsYield
With perchloric acid; d(4)-methanol at 75℃; for 24h; Inert atmosphere;100%
With tris(pentafluorophenyl)borate; water-d2 In chloroform-d1 at 80℃; for 24h; Sealed tube; regioselective reaction;95%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

2-iodomelatonin

2-iodomelatonin

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane at 20℃; for 8h; Inert atmosphere;98%
With chloroamine-T; potassium iodide In chloroform for 0.0833333h;87%
With iodine; silver trifluoromethanesulfonate In tetrahydrofuran at 20℃; for 0.333333h;46%
2-bromo-pyridine
109-04-6

2-bromo-pyridine

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

N-(2-(5-methoxy-1-(pyridin-2-yl)-1H-indol-3-yl)ethyl)acetamide

N-(2-(5-methoxy-1-(pyridin-2-yl)-1H-indol-3-yl)ethyl)acetamide

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 120℃; for 20h; Inert atmosphere;98%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

N-[2-(1-tert-butoxycarbonyl-5-methoxy-1H-indol-3-yl)ethyl]acetamide
431074-74-7

N-[2-(1-tert-butoxycarbonyl-5-methoxy-1H-indol-3-yl)ethyl]acetamide

Conditions
ConditionsYield
With dmap In acetonitrile at 25℃; for 16h;95%
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 0℃; for 0.5h;
Stage #2: di-tert-butyl dicarbonate In dichloromethane at 0℃; for 1h; Further stages.;
80%
With dmap In tetrahydrofuran70%
Stage #1: 5-methoxy-N-acetyl-tryptamine With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In dichloromethane at 20℃; for 5h; Inert atmosphere;
1.13 g
N-(phenylthio)succinimide
14204-24-1

N-(phenylthio)succinimide

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

N-(2-(5-methoxy-2-(phenylthio)-1H-indol-3-yl)ethyl)acetamide

N-(2-(5-methoxy-2-(phenylthio)-1H-indol-3-yl)ethyl)acetamide

Conditions
ConditionsYield
With 2-((-2-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)cyclohexyl)carbamoyl)-3,4,5,6-tetrachlorobenzoic acid; trifluoroacetic acid In methanol; dichloromethane; water at 20℃; for 24h;95%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester
519186-54-0

3-(2-acetylamino-ethyl)-5-methoxy-indole-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 20℃; for 1h;93%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

iodoundecafluorocyclohexane
355-69-1

iodoundecafluorocyclohexane

N-(2-(5-methoxy-2-(perfluorocyclohexyl)-1H-indol-3-yl)ethyl)acetamide

N-(2-(5-methoxy-2-(perfluorocyclohexyl)-1H-indol-3-yl)ethyl)acetamide

Conditions
ConditionsYield
With palladium diacetate; silver carbonate In 1,4-dioxane at 80℃; for 10h; Schlenk technique; Inert atmosphere; regioselective reaction;93%
formic acid
64-18-6

formic acid

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

Nb-acetyl-1-formyl-5-methoxytryptamine

Nb-acetyl-1-formyl-5-methoxytryptamine

Conditions
ConditionsYield
In water at 20℃; for 94h; Formylation;92%
Acylation;88%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

acetic anhydride
108-24-7

acetic anhydride

Nb,Nb-diacetyl-5-methoxytryptamine
188396-98-7

Nb,Nb-diacetyl-5-methoxytryptamine

Conditions
ConditionsYield
for 2h; Acetylation; Heating;92%
2-phenyl-indole
948-65-2

2-phenyl-indole

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

N-(2-(5-methoxy-2-(3-oxo-2-phenylindolin-2-yl)-1H-indol-3-yl)ethyl)acetamide

N-(2-(5-methoxy-2-(3-oxo-2-phenylindolin-2-yl)-1H-indol-3-yl)ethyl)acetamide

Conditions
ConditionsYield
With C9H18NO(1+)*BH4(1-) In tetrahydrofuran at 0℃;92%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

N-propanoyl 2-[1-(2-bromobenzyl)-5-methoxyindol-3-yl]ethanamine

N-propanoyl 2-[1-(2-bromobenzyl)-5-methoxyindol-3-yl]ethanamine

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 20℃; for 3h; Condensation;91%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide
1020701-51-2

N-(2-{5-methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}ethyl)acetamide

Conditions
ConditionsYield
Stage #1: 5-methoxy-N-acetyl-tryptamine With tetrabutylammomium bromide; sodium hydroxide In dichloromethane at 20℃; for 0.5h;
Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 6h;
90.5%
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium hydride In N,N-dimethyl-formamide at 0℃; Inert atmosphere;
Stage #2: p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 0 - 20℃;
Stage #1: 5-methoxy-N-acetyl-tryptamine With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: p-toluenesulfonyl chloride In dichloromethane at 20℃; for 5h; Inert atmosphere;
1.20 g
With tetra(n-butyl)ammonium hydrogensulfate; potassium hydroxide In dichloromethane at 0 - 20℃;
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

2-[131I]-iodo-melatonine

2-[131I]-iodo-melatonine

Conditions
ConditionsYield
With sodium hydroxide; [131I]-sodium iodide; chloroamine-T In chloroform for 0.05h;90%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

ethyl (3-(2-(acetylamino)ethyl)-5-methoxy-1H-indol-2-yl)acetate

ethyl (3-(2-(acetylamino)ethyl)-5-methoxy-1H-indol-2-yl)acetate

Conditions
ConditionsYield
With tris(bipyridine)ruthenium(II) dichloride hexahydrate In methanol; dichloromethane; water Sealed tube; Irradiation; Cooling with ice; regioselective reaction;90%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

Trifluoro-acetic acid (2S,3'S)-5-methoxy-2'-methylene-1,1'-bis-(2,2,2-trifluoro-acetyl)-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-2-yl ester
83345-85-1, 140427-20-9

Trifluoro-acetic acid (2S,3'S)-5-methoxy-2'-methylene-1,1'-bis-(2,2,2-trifluoro-acetyl)-1,2-dihydro-spiro[indole-3,3'-pyrrolidin]-2-yl ester

Conditions
ConditionsYield
In benzene at 5℃; for 0.166667h;89%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

2-(5-methoxyindol-3-yl)ethylamine
608-07-1

2-(5-methoxyindol-3-yl)ethylamine

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 100℃; for 7h; Microwave irradiation;89%
With sulfuric acid In water for 8h; Heating;69.7%
With sodium hydroxide In 2-methyl-propan-1-ol
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-[2-(1-benzenesulfonyl-5-methoxy-1H-indol-3-yl)ethyl]acetamide
296280-80-3

N-[2-(1-benzenesulfonyl-5-methoxy-1H-indol-3-yl)ethyl]acetamide

Conditions
ConditionsYield
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 0℃; for 0.5h;
Stage #2: benzenesulfonyl chloride In dichloromethane at 0℃; for 1h; Further stages.;
88%
Stage #1: 5-methoxy-N-acetyl-tryptamine With sodium hydroxide; tetra-(n-butyl)ammonium iodide at 0℃; for 0.25h;
Stage #2: benzenesulfonyl chloride at 20℃; for 3.5h;
71%
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

C13H28O4Si

C13H28O4Si

isovaleraldehyde
590-86-3

isovaleraldehyde

C25H38N2O6

C25H38N2O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.166667h; chemoselective reaction;88%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.166667h;88%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

4-methoxy-3-(4-(2,2,2-trichloro-acetyl)piperazin-1-yl)benzene-1-sulfonylchloride
219963-60-7

4-methoxy-3-(4-(2,2,2-trichloro-acetyl)piperazin-1-yl)benzene-1-sulfonylchloride

N-(2-(5-methoxy-1-((4-methoxy-3-(4-(2,2,2-trichloroacetyl)piperazin-1-yl)phenyl)sulfonyl)-1H-indol-3-yl)ethyl)acetamide

N-(2-(5-methoxy-1-((4-methoxy-3-(4-(2,2,2-trichloroacetyl)piperazin-1-yl)phenyl)sulfonyl)-1H-indol-3-yl)ethyl)acetamide

Conditions
ConditionsYield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2.16h;88%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

O,O'-bis[(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]-hept-3-yl]dithiophosphoric acid
1456553-31-3

O,O'-bis[(1S,2S,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]-hept-3-yl]dithiophosphoric acid

C20H35O2PS2*C13H16N2O2

C20H35O2PS2*C13H16N2O2

Conditions
ConditionsYield
In ethanol at 20℃; for 1h; Inert atmosphere;88%
5-methoxy-N-acetyl-tryptamine
73-31-4

5-methoxy-N-acetyl-tryptamine

O,O-di[(–)-(1R,2S,5R)-2-isopropyl-5-methylcyclohex-1-yl] dithiophosphoric acid

O,O-di[(–)-(1R,2S,5R)-2-isopropyl-5-methylcyclohex-1-yl] dithiophosphoric acid

C20H39O2PS2*C13H16N2O2

C20H39O2PS2*C13H16N2O2

Conditions
ConditionsYield
In ethanol at 20℃; for 2h; Inert atmosphere;87%

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