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5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole is a complex chemical compound that belongs to the class of pyridine and indole derivatives. It is known for its potential pharmacological properties, particularly as an antipsychotic and anxiolytic agent, and is widely used in organic synthesis and medicinal chemistry.

524-81-2

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524-81-2 Usage

Uses

Used in Pharmaceutical Industry:
5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole is used as a potential antipsychotic agent for the treatment of various mental disorders. Its unique molecular structure allows it to interact with specific receptors in the brain, helping to regulate neurotransmitter levels and alleviate symptoms associated with psychosis.
Used in Anxiolytic Applications:
In addition to its antipsychotic properties, 5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole is also being explored as an anxiolytic agent. It may help to reduce anxiety levels by modulating the activity of certain neurotransmitters, providing a potential therapeutic option for individuals suffering from anxiety disorders.
Used in Organic Synthesis:
5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole is utilized in organic synthesis as a key intermediate in the production of various pharmaceuticals and other chemical compounds. Its unique structure allows for the formation of a wide range of derivatives, making it a valuable building block in the synthesis of new and innovative molecules.
Used in Medicinal Chemistry Research:
As a pyridine and indole derivative, 5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole is of interest to researchers in medicinal chemistry. Its potential pharmacological properties and unique molecular structure make it a promising candidate for further investigation and development as a therapeutic agent for various conditions.

Check Digit Verification of cas no

The CAS Registry Mumber 524-81-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,2 and 4 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 524-81:
(5*5)+(4*2)+(3*4)+(2*8)+(1*1)=62
62 % 10 = 2
So 524-81-2 is a valid CAS Registry Number.
InChI:InChI=1/C19H20N2.C10H8O6S2/c1-20-12-11-19-17(14-20)16-9-5-6-10-18(16)21(19)13-15-7-3-2-4-8-15;11-17(12,13)9-5-1-3-7-8(9)4-2-6-10(7)18(14,15)16/h2-10H,11-14H2,1H3;1-6H,(H,11,12,13)(H,14,15,16)

524-81-2Synthetic route

mebhydroline 1,5-naphtalenedisulfonate

mebhydroline 1,5-naphtalenedisulfonate

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
With sodium hydroxide97%
3-methyl-9-benzyl-γ-carbolinium chloride

3-methyl-9-benzyl-γ-carbolinium chloride

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 24h;73%
1-Methyl-4-piperidone
1445-73-4

1-Methyl-4-piperidone

N-benzyl-N-phenylhydrazine
614-31-3

N-benzyl-N-phenylhydrazine

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
With hydrogenchloride
With sulfuric acid
benzyl chloride
100-44-7

benzyl chloride

sodium-compound of pentadiene-(1.3)

sodium-compound of pentadiene-(1.3)

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / propan-2-ol / 3.5 h / Heating
2: 73 percent / NaBH4 / aq. ethanol / 24 h / 20 °C
View Scheme
2-methyl-2H-pyrido[4,3-b]indole
115191-20-3

2-methyl-2H-pyrido[4,3-b]indole

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / propan-2-ol / 3.5 h / Heating
2: 73 percent / NaBH4 / aq. ethanol / 24 h / 20 °C
View Scheme
1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester
13221-89-1, 56026-45-0

1-methyl-4-oxo-piperidine-3-carboxylic acid methyl ester

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water / 5.17 h / Reflux
2: 10 h / Reflux
View Scheme
1-methylpiperidin-4-one hydrochloride
34737-83-2

1-methylpiperidin-4-one hydrochloride

N-benzyl-N-phenylhydrazine
614-31-3

N-benzyl-N-phenylhydrazine

mebhydrolin
524-81-2

mebhydrolin

Conditions
ConditionsYield
for 10h; Time; Reflux;
methyl bromide
74-83-9

methyl bromide

mebhydrolin
524-81-2

mebhydrolin

5-Benzyl-2,3,4,5-tetrahydro-2,2-dimethyl-1H-pyrido[4,3-b]indol-2-ium-bromid

5-Benzyl-2,3,4,5-tetrahydro-2,2-dimethyl-1H-pyrido[4,3-b]indol-2-ium-bromid

Conditions
ConditionsYield
In ethanol for 18h; cooling;94%
mebhydrolin
524-81-2

mebhydrolin

chloroacetonitrile
107-14-2

chloroacetonitrile

5-benzyl-2-cyanomethyl-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-2-ium chloride

5-benzyl-2-cyanomethyl-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-2-ium chloride

Conditions
ConditionsYield
In tetrahydrofuran at 20℃;92%
mebhydrolin
524-81-2

mebhydrolin

ethyl bromoacetate
105-36-2

ethyl bromoacetate

5-benzyl-2-(2-ethoxy-2-oxoethyl)-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-2-ium bromide

5-benzyl-2-(2-ethoxy-2-oxoethyl)-2-methyl-2,3,4,4a,5,9b-hexahydro-1H-pyrido[4,3-b]indol-2-ium bromide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 48h;91%
mebhydrolin
524-81-2

mebhydrolin

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

Conditions
ConditionsYield
With dihydrogen peroxide In methanol Heating;86%
mebhydrolin
524-81-2

mebhydrolin

sodium 1,5-naphthalenedisulfonate

sodium 1,5-naphthalenedisulfonate

bis-(5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole) naphtalene-1,5-disulfonate

bis-(5-benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole) naphtalene-1,5-disulfonate

Conditions
ConditionsYield
In water at 40℃; for 2h;78%
mebhydrolin
524-81-2

mebhydrolin

acetic acid
64-19-7

acetic acid

2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine
73982-43-1

2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine

2-acetamido-N-[(9-benzyl-3-methyl-1,2,3,4-tetrahydro-3-carbolinium)acetyl]-2-deoxy-β-D-glucopyranosylamine acetate

2-acetamido-N-[(9-benzyl-3-methyl-1,2,3,4-tetrahydro-3-carbolinium)acetyl]-2-deoxy-β-D-glucopyranosylamine acetate

Conditions
ConditionsYield
Stage #1: mebhydrolin; 2-acetamido-1-N-(bromoacetyl)-2-deoxy-β-D-glucopyranosylamine In methanol at 20℃; for 16h;
Stage #2: acetic acid In methanol; water
66%
mebhydrolin
524-81-2

mebhydrolin

A

1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione
210408-31-4

1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione

B

5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

C

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on
210408-29-0

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on

D

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

E

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

Conditions
ConditionsYield
With sodium periodate In methanol for 24h; Product distribution; Mechanism; Ambient temperature; var. of reagent, temp., ratio, solvent, time;A 18%
B 10%
C 12%
D 10%
E 23%
With sodium periodate In methanol; water for 24h; Product distribution; Mechanism; Ambient temperature; var. of reagent, temp., solvent, ratio, time;A 18%
B 10%
C 12%
D 10%
E 23%
mebhydrolin
524-81-2

mebhydrolin

A

1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione
210408-31-4

1-Benzyl-5-methyl-4,5-dihydro-1H,3H-benzo[b][1,5]diazocine-2,6-dione

B

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on
210408-29-0

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on

C

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

5-Benzyl-2-methyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole 2-oxide

D

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

1-Benzyl-1'-methyl-spiro[indolin-2,3'-pyrrolidin]-3-on-1'-oxid

Conditions
ConditionsYield
With sodium periodate In methanol for 24h; Ambient temperature; Further byproducts given;A 18%
B 12%
C 10%
D 23%
With sodium periodate In methanol; water for 24h; Ambient temperature; Further byproducts given;A 18%
B 12%
C 10%
D 23%
mebhydrolin
524-81-2

mebhydrolin

benzyl chloride
100-44-7

benzyl chloride

2,5-dibenzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; chloride
119482-83-6

2,5-dibenzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; chloride

Conditions
ConditionsYield
With acetone
mebhydrolin
524-81-2

mebhydrolin

dimethyl sulfate
77-78-1

dimethyl sulfate

5-benzyl-2,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; methyl sulfate
112049-25-9

5-benzyl-2,2-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indolium; methyl sulfate

Conditions
ConditionsYield
With acetone
mebhydrolin
524-81-2

mebhydrolin

potassium cyanide
151-50-8

potassium cyanide

5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-1-carbonitrile
210408-36-9

5-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-1-carbonitrile

Conditions
ConditionsYield
With maleic acid; palladium 2) H2O; Yield given. Multistep reaction;
With maleic acid; palladium 1) heating, 2) H2O; Yield given. Multistep reaction;
mebhydrolin
524-81-2

mebhydrolin

5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

5-Benzyl-2-methyl-5H-pyrido[4,3-b]indol-2-ium; perchlorate

Conditions
ConditionsYield
With lead(IV) acetate; perchloric acid 1) CHCl3, 1 h; Yield given. Multistep reaction;
With lead(IV) acetate; perchloric acid 1) CHCl3, 1 h, 2) CHCl3; Yield given. Multistep reaction;
Multi-step reaction with 3 steps
1: 1) maleic acid / 1) Pd / 1) heating, 2) H2O
2: 92 percent / HClO4 / ethanol
3: 17 percent / aq. NaOH / 18 h
View Scheme
Multi-step reaction with 3 steps
1: 1) maleic acid / 1) Pd / 2) H2O
2: 92 percent / HClO4 / ethanol
3: 17 percent / aq. NaIO4, NaOH / 18 h
View Scheme
mebhydrolin
524-81-2

mebhydrolin

5-Benzyl-2-methyl-4,5-dihydro-3H-pyrido[4,3-b]indol-2-ium; perchlorate

5-Benzyl-2-methyl-4,5-dihydro-3H-pyrido[4,3-b]indol-2-ium; perchlorate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) maleic acid / 1) Pd / 1) heating, 2) H2O
2: 92 percent / HClO4 / ethanol
View Scheme
Multi-step reaction with 2 steps
1: 1) maleic acid / 1) Pd / 2) H2O
2: 92 percent / HClO4 / ethanol
View Scheme

524-81-2Relevant academic research and scientific papers

Preparation method of mebhydrolin napadisylate

-

Paragraph 0023; 0028; 0029; 0030; 0035; 0036, (2019/06/30)

The invention belongs to the field of drug synthesis and provides a preparation method of mebhydrolin napadisylate. The preparation method is characterized by including the steps of firstly, subjecting methyl imine-N,N-methyl dipropionate and sodium methylate to heating under the effect of an organic solvent to achieve loop closing, and using hydrochloric acid to performing heating decarboxylationto obtain N-methyl-4-piperidone hydrochloride; subjecting phenylhydrazine and benzyl chloride to condensation under an alkaline condition to obtain benzyl phenylhydrazine; thirdly, mixing the N-methyl-4-piperidone hydrochloride solution and the benzyl phenylhydrazine, heating to generate mebhydrolin hydrochloride, adding disodium 1,5-naphthalenedisulfonate to obtain the mebhydrolin napadisylate.The preparation method is high in yield, mild in reaction conditions, convenient in intermediate purification and capable of satisfying the requirements of industrial production.

Indole cleavage with mebhydroline by sodium periodate: Part 1: Basic substituted indoles

Moehrle,Nestle,Westle

, p. 445 - 452 (2007/10/03)

The reaction behaviour of yohimbine (1), reserpine (5) and mebhydroline (7) as basic substituted indoles against periodate was examined. While 1 and 5 gave only the corresponding amine oxides 2 resp. 6 as definitive products, resulted from 7 beside the N-oxide 8 and stepwise dehydrogenation of the tetrahydro-γ-carboline to 9 and 13 also an attack at the indole system. In this ring contractions led to the spiro compounds 10 and 12 and with ring cleavage and loss of a C-1-unit the dilactam 11 was created.

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