770-05-8

Basic information

• Product Name: DL-Octopamine hydrochloride
• Synonyms: dl-octopamine;OCTAPAMINE HCL;OCTOPAMINE HCL;(+/-)-OCTOPAMINE HYDROCHLORIDE;OCTOPAMINE HYDROCHLORIDE;P-(+/-)-ALPHA-(AMINOMETHYL)HYDROXYBENZYL ALCOHOL, HCL;P-HYDROXYPHENYLAMINOETHANOL HYDROCHLORIDE;DL-OCTOPAMINE HYDROCHLORIDE
• CAS NO: 770-05-8
• Molecular Formula: C₈H₁₂NO₂*Cl
• Molecular Weight: 189.64
• EINECS: 212-216-4
• Product Categories: Miscellaneous Natural Products;Adrenoceptor;Amines;Aromatics;Neurochemicals;Pharma raw material
• Mol File: 770-05-8.mol

Chemical Properties

• Melting Point: ~170 °C (dec.)(lit.)
• Boiling Point: 360.7 °C at 760 mmHg
• Flash Point: 172 °C
• Appearance: white or off-white/solid
• Density: 1.39[at 20℃]
• Vapor Pressure: 7.82E-06mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: H2O: soluble
• Water Solubility: soluble
• Stability: Stable.
• Merck: 13,6791
• BRN: 3915414
• CAS DataBase Reference: DL-Octopamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: DL-Octopamine hydrochloride(770-05-8)
• EPA Substance Registry System: DL-Octopamine hydrochloride(770-05-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-37/39-26
• RIDADR: 3249
• WGK Germany: 3
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 770-05-8(Hazardous Substances Data)

Usage

Uses

Used in Bodybuilding Industry:
DL-Octopamine hydrochloride is used as an ephedrine alternative for weight loss purposes. It helps to maximize adipose loss while minimizing the loss of muscle and other lean body tissue during weight loss. It is known to boost energy and reduce weight, making it a popular choice in the bodybuilding industry.
Used in Nootropic Applications:
Many users believe that DL-Octopamine hydrochloride is a good nootropic compound. It is used to enhance focus and motivation, acting as a wakefulness promoter, which can be beneficial for individuals seeking cognitive enhancement.
Used in Neurotransmission Regulation:
As a neurotransmitter, neuromodulator, and neurohormone, DL-Octopamine hydrochloride is used to regulate various behaviors, such as learning, memory, and aggression. It plays a crucial role in the nervous system of both mammals and invertebrates.
Used in Pharmaceutical Industry:
DL-Octopamine hydrochloride, due to its adrenergic properties, is used in the pharmaceutical industry for the development of drugs targeting adrenergic alpha-receptors. Its vasoconstrictive and hypertensive effects make it a potential candidate for the treatment of certain medical conditions.

Flammability and Explosibility

Notclassified

Biological Activity

Invertebrate biogenic amine neurotransmitter, related to noradrenalin, that is an adrenoceptor agonist. Stimulates lipolysis in mammalian adipocytes via activation of β 3 receptors. Has dual effect on glucose transport in adipocytes: inhibits transport via β 3 receptor activation but stimulates transport when oxidised by MAO. Also activates human α 2A receptors, inhibiting subsequent cAMP production.

Mode of action

Octopamine hydrochloride is an invertebrate biogenic amine neurotransmitter, related to noradrenalin, that is an adrenoceptor (AR) agonist. Octopamine hydrochloride stimulates lipolysis in mammalian adipocytes via activation of β3-AR receptors. Has dual effect on glucose transport in adipocytes: inhibits transport via β3-AR receptor activation but stimulates transport when oxidised by MAO. Also activates human α2A-AR receptors, inhibiting subsequent cAMP production.

InChI:InChI=1/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2/p+1/t8-/m0/s1

Synthetic route

C8H11NO2*C7H8N2O*2ClH → octopamine hydrochloride (770-05-8) + N-methylnicotinamide hydrochloride (29711-57-7)

Conditions	Yield
at 28℃; Equilibrium constant; Thermodynamic data; association enthalpy: ΔH0 (kcal mol-1) = -2.6 (pH=1); -2.3 (pH=7);

octopamine hydrochloride (770-05-8) + tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate (145013-05-4) → C19H29N3O6 (1037078-73-1, 1427086-29-0)

Conditions	Yield
With triethylamine; mercury dichloride In DMF (N,N-dimethyl-formamide)	99%

di-tert-butyl dicarbonate (24424-99-5) + octopamine hydrochloride (770-05-8) → tert-butyl (2-hydroxy-2-(4-hydroxyphenyl)ethyl)carbamate (126395-31-1)

Conditions	Yield
With sodium hydrogencarbonate In methanol; water	85%
With triethylamine In methanol at 20℃;	80%
With sodium hydroxide In water; tert-butyl alcohol at 20℃; for 16h;	56%

octopamine hydrochloride (770-05-8) + N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-54-2, 862686-58-6, 1143572-00-2) → tert-butyl [(Z)-[(tert-butoxycarbonyl)amino]{[2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino}methylidene]carbamate (1037078-73-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;	81.4%

N-ethoxycarbonylphthalimide (22509-74-6) + octopamine hydrochloride (770-05-8) → 4-(2-N-phthaloyl-1-hydroxyethyl)phenol

Conditions	Yield
With sodium carbonate In water	81%

octopamine hydrochloride (770-05-8) + 4-O-(β-D-galactopyranosyl)-N-chloroacetyl-β-D-glucopyranosylamine (183583-61-1) → N-{N-[DL-2-hydroxy-2-(4-hydroxyphenyl)ethyl]glycyl}-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosylamine

Conditions	Yield
With triethylamine In methanol; dimethyl sulfoxide at 70℃; for 22h; Alkylation;	79%

octopamine hydrochloride (770-05-8) + (Z)-tert-butyl (((tert-butoxycarbonyl)imino)(1H-pyrazol-1-yl)methyl)carbamate (152120-54-2, 862686-58-6, 1143572-00-2) → tert-butyl [(Z)-[(tert-butoxycarbonyl)amino]{[2-hydroxy-2-(4-hydroxyphenyl)ethyl]amino}methylidene]carbamate (1037078-73-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h;	73%

2,3-dihydroxybenzaldehyde (24677-78-9) + octopamine hydrochloride (770-05-8) → C15H15NO4

Conditions	Yield
With triethylamine In methanol at 20℃; for 3h;	70.2%

N-butoxycarbonyl-(L)-valine + octopamine hydrochloride (770-05-8) → E-L-Val-p-(2-aminoethenyl)phenol

Conditions	Yield
Stage #1: N-butoxycarbonyl-(L)-valine; octopamine hydrochloride With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; Stage #2: With pyridine; acetic anhydride at 100℃; for 1h; Further stages;	69%

octopamine hydrochloride (770-05-8) + phenol (108-95-2) → 4,4'-(2-amino-ethylidene)-di-phenol; hydrochloride (3516-08-3)

Conditions	Yield
With hydrogenchloride In Dimethyl ether at 100℃;	68%

palmitic anhydride (623-65-4) + octopamine hydrochloride (770-05-8) → hexadecanoic acid 2-hexadecanoylamino-1-(4-hexadecanoyloxy-phenyl)-ethyl ester

Conditions	Yield
With pyridine at 100℃; for 2.5h;	66%

carbon disulfide (75-15-0) + octopamine hydrochloride (770-05-8) + methyl iodide (74-88-4) → dihydrotridentatol C

Conditions	Yield
With TEA In chloroform for 3h; Heating;	52%

octopamine hydrochloride (770-05-8) + 3-Formylchromone (17422-74-1) → C18H15NO4

Conditions	Yield
With triethylamine In methanol	37.6%

4-[4-(3-Oxobutyl)phenoxy]butanoic acid, ethyl ester (174884-23-2) + octopamine hydrochloride (770-05-8) → 10-O-[3-(ethoxycarbonyl)propyl]ractopamine ether (911196-28-6)

Conditions	Yield
Stage #1: 4-[4-(3-Oxobutyl)phenoxy]butanoic acid, ethyl ester; octopamine hydrochloride With sodium cyanoborohydride; triethylamine In methanol at 50℃; Stage #2: With hydrogenchloride In water	28%

(1S)-10-camphorsulfonic acid (3144-16-9) + octopamine hydrochloride (770-05-8) → (-)-2-amino-1-(4-hydroxyphenyl)ethanol (1S)-(+)camphor-10-sulphonate (1830-39-3)

Conditions	Yield
With Dowex 50W-X8 In ethanol at 4℃; for 12h;	26.7%

(1S)-10-camphorsulfonic acid (3144-16-9) + octopamine hydrochloride (770-05-8) → (+)-2-amino-1-(4-hydroxyphenyl)ethanol (1S)-(+)camphor-10-sulphonate (1693-64-7)

Conditions	Yield
With Dowex 50W-X8 In ethanol at 4℃; for 12h;	20%

3,3-diphenyl-2-propenal (1210-39-5) + octopamine hydrochloride (770-05-8) → 4-{2-[3,3-Diphenyl-prop-2-en-(E)-ylideneamino]-1-hydroxy-ethyl}-phenol

Conditions	Yield
With sodium hydrogencarbonate

octopamine hydrochloride (770-05-8) + 4-amino-3,6-disulfo-1,8-naphthaldehyde anhydride dipotassium salt (79539-35-8) → C20H14N2O10S2(2-)*2K(1+)

Conditions	Yield
In water Heating; pH 5, Li(1+)/H(1+) acetate buffer;

octopamine hydrochloride (770-05-8) + N-methylnicotinamide hydrochloride (29711-57-7) → C8H11NO2*C7H8N2O*2ClH

Conditions	Yield
at 28℃; Equilibrium constant; Thermodynamic data; association enthalpy: ΔH0 (kcal mol-1) = -2.6 (pH=1); -2.3 (pH=7);

octopamine hydrochloride (770-05-8) → (+)p-octopamine hydrochloride (770-05-8, 4502-14-1, 19462-08-9)

octopamine hydrochloride (770-05-8) → (-)p-octopamine hydrochloride (19462-08-9)

octopamine hydrochloride (770-05-8) + benzoyl chloride (98-88-4) → N-benzoyloctopamine (115722-49-1)

Conditions	Yield
With pyridine Yield given;

2-bromoisovanillin (2973-59-3) + octopamine hydrochloride (770-05-8) → p-hydroxy-α-(2-bromo-5-hydroxy-4-methoxybenzylaminomethyl)benzyl alcohol

Conditions	Yield
With sodium tetrahydroborate; sodium hydrogencarbonate 1.) MeOH, 50 deg C, 2 h, 2.) r.t., 1 h; Yield given. Multistep reaction;

octopamine hydrochloride (770-05-8) → serin (302-84-1)

Conditions	Yield
With dihydrogen peroxide; ozone 1.) H2O; Yield given. Multistep reaction;

potassium thioacyanate (333-20-0) + octopamine hydrochloride (770-05-8) → DL-3-Thiocyanatooctopamin

Conditions	Yield
(i) Cl2, AcOH, (ii) /BRN= 3915414/; Multistep reaction;

BOC-glycine (4530-20-5) + octopamine hydrochloride (770-05-8) → {[2-hydroxy-2-(4-hydroxy-phenyl)-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 25℃; for 17h; Acylation;

octopamine hydrochloride (770-05-8) + 2-benzyl-3-chloro-3-phenyl-2,3-dihydroisoindol-1-one (237769-24-3) → 2-benzyl-3-[2-hydroxy-2-(4-hydroxyphenyl)ethylamino]-3-phenyl-2,3-dihydroisoindol-1-one

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 20h;	0.27 g

octopamine hydrochloride (770-05-8) + Mmt-chloride (383401-15-8) → C31H31NO4S (865871-05-2)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.833333h;

octopamine hydrochloride (770-05-8) → tridentatol C

Conditions	Yield
Multi-step reaction with 2 steps 1: 52 percent / TEA / CHCl3 / 3 h / Heating 2: DDQ / CHCl3 / 3 h / Heating View Scheme

octopamine hydrochloride (770-05-8) → Hexadecanoic acid [(E)-2-(4-hydroxy-phenyl)-vinyl]-amide

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / pyridine / 2.5 h / 100 °C 2: 43 percent / potassium carbonate; dimethyl sulfoxide / dimethylformamide / 5 h / 100 °C View Scheme

Downstream Products

• 1830-39-3 (-)-2-amino-1-(4-hydroxyphenyl)ethanol (1S)-(+)camphor-10-sulphonate 
• 1693-64-7 (+)-2-amino-1-(4-hydroxyphenyl)ethanol (1S)-(+)camphor-10-sulphonate 
• 770-05-8 (+)p-octopamine hydrochloride 
• 115722-49-1 N-benzoyloctopamine 
• 302-84-1 serin 
• 3516-08-3 4,4'-(2-amino-ethylidene)-di-phenol; hydrochloride 
• 865871-05-2 C₃₁H₃₁NO₄S 
• 262601-13-8 (E)-N-[2-(4-hydroxyphenyl)ethenyl]glycinamide 
• 262601-06-9 (E)-N-[2-(4-acetoxyphenyl)ethenyl]glycinamide 
• 262601-04-7 {[2-(4-hydroxy-phenyl)-vinylcarbamoyl]-methyl}-carbamic acid tert-butyl ester 
• 262601-05-8 (E)-N-[2-(4-acetoxyphenyl)ethenyl](Boc)glycinamide 

Relevant articles and documents

The Resolution and Absolute Configuration by X-Ray Crystallography of the Isomeric Octopamines and Synephrines

Racemates of the naturally occuring biogenic amines, o-, m-, and p-octopamine and p-synephrine, have been resolved by the preparation of suitable diastereomeric salts with antipodes of appropriate organic acids.The circular dichroism (c.d.) curves of (-)-m-octopamine hydrochloride and (-)-m-synephrine hydrochloride were superimposable and of opposite sign to those of the corresponding (-)-p-derivatives.X-ray crystallography of the (-)-3-bromocamphor-8-sulphonate salt of (-)-p-synephrine confirmed (for the first time by direct means in this series of compounds) that the absolute configuration of (-)-p-synephrine is R.It is concluded from the c.d. data that the absolute configuration of (-)-p-octopamine is also R.