131-03-3

Basic information

• Product Name: alpha-yohimbine
• Synonyms: methyl (16beta,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate;4-(2-amino-1-hydroxyethyl)-2-methoxyphenol hydrochloride(1:1)
• CAS NO: 131-03-3
• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.44274
• EINECS: 205-006-9
• Mol File: 131-03-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 243-244°
• Boiling Point: 543°Cat760mmHg
• Flash Point: 282.2°C
• Appearance: /
• Density: 1.31g/cm³
• Vapor Pressure: 0mmHg at 25°C
• PKA: 6.34(at 25℃)
• CAS DataBase Reference: alpha-yohimbine(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-yohimbine(131-03-3)
• EPA Substance Registry System: alpha-yohimbine(131-03-3)

Safety Data

• RIDADR: 1544
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 131-03-3(Hazardous Substances Data)

Usage

General Description

Alpha-yohimbine, also known as rauwolscine, is a chemical compound found in the bark of the yohimbe tree. It is a stereoisomer of yohimbine and is known to have similar, but potentially more potent, effects. Alpha-yohimbine acts as an alpha-2 adrenergic receptor antagonist, which means that it can block the receptors for the neurotransmitter norepinephrine. This can potentially lead to increased levels of norepinephrine in the body, which may in turn have stimulating effects and potentially aid in weight loss and erectile dysfunction. However, it is important to note that alpha-yohimbine, like yohimbine, may also have potential side effects and risks, and should be used with caution and under the guidance of a healthcare professional.

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/p+1/t12-,15+,17+,18+,19+/m1/s1

Upstream product

• 1218-41-3 1-<2-(1H-indol-3-yl)ethyl>-4-piperidinone 
• 37734-07-9 methyl endo/exo-3-(bicyclo<2,2,1>hept-5-en-2-yl)-3-oxopropanoate 
• 26822-37-7 N,N-dimethyl-4-oxopiperidinium iodide 
• 37734-05-7 Methyl 3-oxo-4-pentenoate 
• 61-54-1 tryptamine 
• 2114-90-1 methyl (16α)-17-oxoyohimban-16-carboxylate 
• 88966-92-1 dimethyl (16α)-17-oxoyohimban-1,16-dicarboxylate 
• 54725-64-3 (20β)-18,19-didehydroyohimban-17-one 
• 81750-86-9 19,20-didehydroyohimban-17-one 
• 2671-54-7 methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate 
• 7732-18-5 water 
• 10035-10-6 hydrogen bromide 
• 483-09-0 Isorauhimbine 
• 186581-53-3 diazomethane 

Downstream Products

• 122675-16-5 17α-(toluene-4-sulfonyloxy)-20α-yohimban-16β-carboxylic acid methyl ester 
• 14727-69-6 17α-hydroxy-16β-methoxycarbonyl-4ξ-methyl-20α-yohimbanium; iodide 
• 146-48-5 Yohimbine 
• 65-19-0 rauwolscine hydrochloride 

Relevant articles and documents

Bicyclic Guanidine Catalyzed Asymmetric Tandem Isomerization Intramolecular-Diels-Alder Reaction: The First Catalytic Enantioselective Total Synthesis of (+)-alpha-Yohimbine

Hydroisoquinoline derivatives were prepared in moderate to good enantioselectivities via a bicyclic guanidine-catalyzed tandem isomerization intramolecular-Diels-Alder (IMDA) reaction of alkynes. With this synthetic method, the first enantioselective synthesis of (+)-alpha-yohimbine was completed in 9 steps from the IMDA products.

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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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