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65-19-0

Basic Information
CAS No.: 65-19-0
Name: Yohimbine hydrochloride
Molecular Structure:
Molecular Structure of 65-19-0 (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: ToxicT
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
ConditionsYield
With sodium cyanoborohydride In trifluoroacetic acid100%
With sodium cyanoborohydride In trifluoroacetic acid at 20℃; for 3h;100%
65-19-0

yohimbine

366456-76-0

1-hydroxyyohimbine

Conditions
ConditionsYield
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
ConditionsYield
With sodium persulfate; hydrogen fluoride; antimony pentafluoride at -35℃; for 1h;A 32 % Chromat.
B 23 % Chromat.
C 11 % Chromat.
D 3 % Chromat.
65-19-0

yohimbine

1-propargyloxyyohimbine

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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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    65-19-0 - Physico-chemical Properties Molecular Formula C21H27ClN2O3 Molar Mass 390.9 Melting Point 288-290°C (dec.)(lit.) Boling Point 542.979°C at 760 mmHg Specific Rotation(α)

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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.