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Basic Information

Molecular Structure:
CAS No.:	65-19-0
Name:	Yohimbine hydrochloride

Formula:	C₂₁H₂₆N₂O₃.ClH
Molecular Weight:	390.91
Synonyms:	Yohimban-16-carboxylicacid, 17-hydroxy-, methyl ester, monohydrochloride, (16a,17a)- (9CI);Yohimban-16a-carboxylic acid, 17a-hydroxy-, methyl ester, monohydrochloride (8CI);Actibine;Antagonil;Yohimbe;Yohimbine monohydrochloride;Yohimex;Yohimbe Bark Extract;Yohimbine hydrochloride;
EINECS:	200-600-4
Melting Point:	288-290 °C (dec.)(lit.)
Boiling Point:	543 °C at 760 mmHg
Flash Point:	282.2 °C
Appearance:	Very slightly yellow needles.
Hazard Symbols:	T
Risk Codes:	23/24/25-33-23/24
Safety:	22-36/37/39-45-24/25
PSA:	65.56000
LogP:	3.38700

Synthetic route

: 65-19-0
yohimbine

: 142696-96-6
2α,7α-dihydroyohimbine

Conditions

Conditions	Yield
With sodium cyanoborohydride In trifluoroacetic acid	100%
With sodium cyanoborohydride In trifluoroacetic acid at 20℃; for 3h;	100%

: 65-19-0
yohimbine

: 366456-76-0
1-hydroxyyohimbine

Conditions

Conditions	Yield
Stage #1: yohimbine With sodium cyanoborohydride In trifluoroacetic acid at 20℃; for 3h; Stage #2: With sodium tungstate; dihydrogen peroxide In methanol; water at 0℃; for 1h; Further stages.;	86%
Multi-step reaction with 2 steps 1: 100 percent / NaBH3CN / trifluoroacetic acid 2: 86 percent / Na2WO4*2H2O; 30 percent H2O2 View Scheme

: 65-19-0
yohimbine

A: 41928-02-3
10-hydroxy-yohimbine

B: 11-hydroxy-yohimbine

C: 9-Hydroxyyohimbine

D: 12-Hydroxyyohimbine

Conditions

Conditions	Yield
With sodium persulfate; hydrogen fluoride; antimony pentafluoride at -35℃; for 1h;	A 32 % Chromat. B 23 % Chromat. C 11 % Chromat. D 3 % Chromat.

...Expand

: 65-19-0
yohimbine

: 1-propargyloxyyohimbine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C 1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C 2.1: 99 percent / K2CO3 / dimethylformamide / 0.5 h / 20 °C View Scheme

: 65-19-0
yohimbine

: 1-isopropyloxyyohimbine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C 1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C 2.1: Cs2CO3 / methanol / 0.33 h / 20 °C 2.2: 99 percent / dimethylformamide / 1 h / 20 °C View Scheme

: 65-19-0
yohimbine

: (dl)-1-(1-methoxycarbonyl)ethoxyyohimbine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C 1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C 2.1: Cs2CO3 / methanol / 0.33 h / 20 °C 2.2: 99 percent / dimethylformamide / 1 h / 20 °C View Scheme

: 65-19-0
yohimbine

: 1-cyclohexyloxyyohimbine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C 1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C 2.1: Cs2CO3 / methanol / 0.33 h / 20 °C 2.2: 11 percent / dimethylformamide / 1 h / 20 °C View Scheme

: 65-19-0
yohimbine

: 142756-69-2
Na-methoxyyohimbine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C 1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C 2.1: 77 percent / methanol; diethyl ether / 1 h / 0 °C View Scheme
Multi-step reaction with 3 steps 1: 100 percent / NaBH3CN / trifluoroacetic acid 2: 86 percent / Na2WO4*2H2O; 30 percent H2O2 3: 77 percent / methanol View Scheme

: 65-19-0
yohimbine

: 1-allyloxyyohimbine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C 1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C 2.1: 99 percent / K2CO3 / dimethylformamide / 0.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 100 percent / NaBH3CN / trifluoroacetic acid 2: 86 percent / Na2WO4*2H2O; 30 percent H2O2 3: 93 percent / K2CO3 / dimethylformamide View Scheme

: 65-19-0
yohimbine

: 1-n-butyloxyyohimbine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C 1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C 2.1: 93 percent / K2CO3 / dimethylformamide / 0.5 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 100 percent / NaBH3CN / trifluoroacetic acid 2: 86 percent / Na2WO4*2H2O; 30 percent H2O2 3: 99 percent / K2CO3 / dimethylformamide View Scheme

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The CAS registry number of Yohimbine hydrochloride is 65-19-0. With the EINECS registry number 200-600-4, the IUPAC name of it is methyl (16α,17α)-17-hydroxyyohimban-16-carboxylate hydrochloride (1:1). In addition, the molecular formula is C₂₁H₂₆N₂O₃.ClH and the molecular weight is 354.44. It is a kind of white to slightly yellow powder and belongs to the classes of Alkaloids; Biochemistry; Indole Alkaloids; Natural Plant Extract; Adrenoceptor; Adrenoceptors. What's more, it is a plant alkaloid with alpha-2-adrenergic blocking activity.

Physical properties about Yohimbine hydrochloride are: (1)ACD/LogP: 2.874; (2)ACD/LogD (pH 5.5): 0.11; (3)ACD/LogD (pH 7.4): 1.72; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 6.33; (6)ACD/KOC (pH 5.5): 1.51; (7)ACD/KOC (pH 7.4): 61.30; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.661; (12)Molar Refractivity: 99.461 cm³; (13)Molar Volume: 269.114 cm³; (14)Polarizability: 39.429 10-24cm³; (15)Surface Tension: 63.3400001525879 dyne/cm; (16)Density: 1.317 g/cm³; (17)Flash Point: 282.184 °C; (18)Enthalpy of Vaporization: 86.429 kJ/mol; (19)Boiling Point: 542.979 °C at 760 mmHg

Uses of Yohimbine hydrochloride: it can be used for biochemical studies. And it is used as a mydriatic and in the treatment of erectile dysfunction. In addition, it can be used to get 2-hydroxy-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester. This reaction will need reagent NaBH₃CN and solvent trifluoroacetic acid. The yield is about 100%.

Yohimbine hydrochloride can be used to get 2-hydroxy-1,2,3,4,4a,5,7,8,8a,13,13a,13b,14,14a-tetradecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

When you are using this chemical, please be cautious about it as the following:
It has danger of cumulative effects. And it is toxic by inhalation, in contact with skin and if swallowed. During using it, wear suitable protective clothing and gloves and eye/face protection and avoid contact with skin and eyes. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). In addition, do not breathe dust.

You can still convert the following datas into molecular structure:
(1)SMILES: Cl.O=C(OC)[C@@H]5[C@H]4C[C@H]3c2nc1ccccc1c2CCN3C[C@@H]4CC[C@@H]5O
(2)InChI: InChI=1/C21H26N2O3.ClH/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;1H/t12-,15-,17-,18-,19+;/m0./s1
(3)InChIKey: PIPZGJSEDRMUAW-VJDCAHTMBF

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LDLo	subcutaneous	20mg/kg (20mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE AUTONOMIC NERVOUS SYSTEM: OTHER (DIRECT) PARASYMPATHOMIMETIC	"Zur Pharmakologie der Yohimbealkaloide, Dissertation," Langer, J., Institute fuer Pharmakologie und Experimentelle Therapie der Universitat Breslau, Poland, 1932Vol. -, Pg. -, 1932.
frog	LD50	parenteral	26mg/kg (26mg/kg)		Bulletin des Sciences Pharmacologiques. Vol. 47, Pg. 33, 1940.
frog	LD50	subcutaneous	34mg/kg (34mg/kg)		Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 137, Pg. 305, 1943.
guinea pig	LD50	intraperitoneal	42mg/kg (42mg/kg)		Bulletin des Sciences Pharmacologiques. Vol. 47, Pg. 33, 1940.
man	TDLo	oral	133ug/kg (.133mg/kg)	BEHAVIORAL: EUPHORIA	American Journal of Psychiatry. Vol. 141, Pg. 1267, 1984.
mouse	LD50	intraperitoneal	45mg/kg (45mg/kg)		United States Patent Document. Vol. #4179510,
mouse	LD50	oral	40mg/kg (40mg/kg)	LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	Journal of Pharmaceutical Sciences. Vol. 51, Pg. 345, 1962.
mouse	LD50	subcutaneous	43900ug/kg (43.9mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	British Journal of Pharmacology and Chemotherapy. Vol. 21, Pg. 51, 1963.
mouse	LDLo	intravenous	15mg/kg (15mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 50, Pg. 241, 1935.
rabbit	LDLo	intravenous	5mg/kg (5mg/kg)		"Zur Pharmakologie der Yohimbealkaloide, Dissertation," Langer, J., Institute fuer Pharmakologie und Experimentelle Therapie der Universitat Breslau, Poland, 1932Vol. -, Pg. -, 1932.
rat	LD50	intraperitoneal	55mg/kg (55mg/kg)	AUTONOMIC NERVOUS SYSTEM: CENTRAL SYMPATHOLYTIC BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 110, Pg. 20, 1957.
women	TDLo	oral	400ug/kg (.4mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: EUPHORIA	American Journal of Psychiatry. Vol. 141, Pg. 1267, 1984.