522-94-1

Basic information

• Product Name: allo-yohimbine
• Synonyms: ALLOYOHIMBINE;(20α)-17α-Hydroxyyohimban-16α-carboxylic acid methyl;(20α)-17α-Hydroxyyohimban-16α-carboxylic acid methyl ester;Dihydroyohimbine
• CAS NO: 522-94-1
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.44
• Mol File: 522-94-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 98-99°; anhydrous form melts at 135-140°
• Boiling Point: 543°Cat760mmHg
• Flash Point: 282.2°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 1.27E-12mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: allo-yohimbine(CAS DataBase Reference)
• NIST Chemistry Reference: allo-yohimbine(522-94-1)
• EPA Substance Registry System: allo-yohimbine(522-94-1)

Safety Data

• Hazardous Substances Data: 522-94-1(Hazardous Substances Data)

Usage

General Description

Allo-yohimbine is a chemical compound that is derived from yohimbine, a naturally occurring alkaloid found in the bark of the yohimbe tree. It is structurally similar to yohimbine and exhibits similar physiological effects, including acting as an alpha-2 adrenergic receptor antagonist. Allo-yohimbine has been studied for its potential use in the treatment of erectile dysfunction, as well as for its effects on metabolism and weight loss. It is also being investigated for its potential as an antidepressant and anxiolytic agent. Research on allo-yohimbine is ongoing, and its full range of pharmacological effects and potential therapeutic applications are still being explored.

InChI:InChI=1/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15+,17+,18+,19-/m1/s1

Upstream product

• 2114-90-1 methyl (16α)-17-oxoyohimban-16-carboxylate 
• 81750-86-9 19,20-didehydroyohimban-17-one 
• 54725-64-3 (20β)-18,19-didehydroyohimban-17-one 
• 88966-92-1 dimethyl (16α)-17-oxoyohimban-1,16-dicarboxylate 
• 61-54-1 tryptamine 
• 37734-05-7 Methyl 3-oxo-4-pentenoate 
• 26822-37-7 N,N-dimethyl-4-oxopiperidinium iodide 
• 92579-46-9 2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4(1H)-pyridinone 
• 37734-07-9 methyl endo/exo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate 
• 132672-75-4 methyl 1,2,6,7,8,8a-hexahydro-2-<2-(1H-indol-3-yl)ethyl>-6-oxo-5-isoquinolinecarboxylate 
• 132672-67-4 2,3-dihydro-1-<2-(1H-indol-3-yl)ethyl>-4-methoxypyridinium trifluoromethanesulfonate 
• 36069-26-8 methyl (20β)-15,16-didehydro-17-oxoyohimban-16-carboxylate 
• 36069-26-8 methyl (20α)-15,16-didehydro-17-oxoyohimban-16-carboxylate 
• 1218-41-3 1-<2-(1H-indol-3-yl)ethyl>-4-piperidinone 

Downstream Products

• 131-03-3 rauwolscine 
• 146-48-5 Yohimbine 

Relevant articles and documents

Total Syntheses of Yohimbe Alkaloids, with Stereoselection for the Normal, Allo, and 3-Epiallo Series, Based on Annelations of 4-Methoxy-1,2-dihydropyridones

N--2,3-dihydro-4-pyridone (31) was generated in two steps (77percent yield) from tryptamine and N-methyl-4-piperidone methiodide.Its cyclization (90percent yield) and oxidation (91percent yield) provided the tetracyclic analogue 32.O-Methylation and Robinson-type annelation of these vinylogous lactams (the latter in form of its Na-carbamate) furnished the dienones 38 (64percent) and 43 (90percent).Further elaboration by cyclization and/or reduction reactions selectively provided the 15,16-didehydroyohimbinones 7 and 44.Their reductions then led to yohimbinone (52, 20percent overall yield from tryptamine), alloyohimbinone (11, 19percent overall yield), and 3-epi-alloyohimbinone (10, 23percent overall yield), which led to yohimbine (3), β-yohimbine (9), 3-epi-alloyohimbine (53), and 3-epi-17-epi-alloyohimbine (54).

Total synthesis of yohimbine.

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