Name: 17alpha-Hydroxy-yohimban-16alpha-carboxylic acid methyl ester
SKU: 146-48-5

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Basic Information

Molecular Structure:
CAS No.:	146-48-5
Name:	17alpha-Hydroxy-yohimban-16alpha-carboxylic acid methyl ester
Article Data:	42

Formula:	C₂₁H₂₆N₂O₃
Molecular Weight:	354.449
Synonyms:	Yohimban-16a-carboxylic acid, 17a-hydroxy-, methyl ester (8CI);Yohimbol-16a-carboxylic acid, methyl ester(6CI);(+)-Yohimbine;Aphrodine;Aphrosol;Corynine;Quebrachin;Quebrachine;Yohimbicacid methyl ester;Yohimbin;Yohimbine;trans-Quinolizidine yohimbine;
EINECS:	205-672-0
Density:	1.31 g/cm³
Melting Point:	231-233 °C(lit.)
Boiling Point:	543 °C at 760 mmHg
Flash Point:	282.2 °C
Hazard Symbols:	T
Risk Codes:	23/24/25-39
Safety:	27-36/37/39-45
PSA:	65.56000
LogP:	2.58500

Synthetic route

: 1011533-78-0
(1R,2S,4aR,13bS,14aS)-methyl-2-hydroxy-1,2,4a,5,7,8,13,13b,14,14a-decahydroindolo[2',3':3,4]pyrido-[1,2-b]isoquinoline-1-carboxylate

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With 10% Pd/C; hydrogen In ethyl acetate for 14h;	100%
With palladium 10% on activated carbon; hydrogen In ethyl acetate under 760.051 Torr; for 15h;	100%

: 2671-57-0
(+)-yohimbinone

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With L-Selectride In tetrahydrofuran at -78℃; for 0.5h;	86%
With sodium tetrahydroborate In isopropyl alcohol Product distribution; Reduction;

: C23H29N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0166667h; Reagent/catalyst; Temperature; Microwave irradiation; stereospecific reaction;	74%

: C25H33N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0833333h; Microwave irradiation; stereospecific reaction;	62%

: C28H31N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0166667h; Microwave irradiation; stereospecific reaction;	59%

: 23943-82-0, 25181-38-8
4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0166667h; Time; Microwave irradiation; stereospecific reaction;	50%

: C28H31N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0166667h; Microwave irradiation; stereospecific reaction;	32%

: C25H33N3O4

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid at 160℃; for 0.0833333h; Microwave irradiation; stereospecific reaction;	17%

: 17α-hydroxy-16α-methoxycarbonyl-yohimba-3,5-dienium; perchlorate

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate

: 17α-hydroxy-16α-methoxycarbonyl-yohimb-3-enium; perchlorate

: 146-48-5
Yohimbine

Conditions

Conditions	Yield
With acetic acid; zinc

Raw Materials

2671-57-0

27856-66-2

549-84-8

483-10-3

84-37-7

522-87-2

18107-18-1

19351-63-4

Downstream Products

525-15-5

30365-50-5

1484-19-1

486-84-0

1477-50-5

119-65-3

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Standards and Recommendations

IDENTITY: Complies
CONTENT: 98.0% min
MOISTURE: 1.0% max
HEAVY METALS: 10ppm max

Specification

The CAS registry number of Yohimbine is 146-48-5. Its EINECS registry number is 205-672-0. The systematic name is methyl (16α,17α)-17-hydroxyyohimban-16-carboxylate. In addition, the molecular formula is C₂₁H₂₆N₂O₃ and the molecular weight is 354.44. What's more, it is an alkaloid with stimulant and aphrodisiac effects found naturally in Pausinystalia yohimbe and belongs to the classes of Adrenoceptor and API.

Physical properties about this chemical are: (1)ACD/LogP: 2.20; (2)ACD/LogD (pH 5.5): -0.56; (3)ACD/LogD (pH 7.4): 1.05; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1.95; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 26.39; (8)#H bond acceptors: 5; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 43.7 Å²; (12)Index of Refraction: 1.66; (13)Molar Refractivity: 99.46 cm³; (14)Molar Volume: 269.1 cm³; (15)Polarizability: 39.42 ×10^-24cm³; (16)Surface Tension: 63.3 dyne/cm; (17)Density: 1.31 g/cm³; (18)Flash Point: 282.2 °C; (19)Enthalpy of Vaporization: 86.43 kJ/mol; (20)Boiling Point: 543 °C at 760 mmHg; (21)Vapour Pressure: 1.27E-12 mmHg at 25°C.

Preparation of Yohimbine: it can be prepared by yohimbinone. The other product is (+/-)-b-yohimbine. This reaction will need reagent sodium borohydride and solvent methanol. The reaction time is 20 minutes at reaction temperature of 0 °C. The yield is about 52.9%.

Yohimbine can be prepared by yohimbinone. The other product is (+/-)-b-yohimbine

Uses of Yohimbine: it has been used to facilitate recall of traumatic memories in the treatment of posttraumatic stress disorder. And it can be used in arteriosclerosis and angina pectoris, and has been used as a local anesthetic and mydriatic and for its purported aphrodisiac properties. In addition, it can be used as both an over-the-counter dietary supplement in herbal extract form and prescription medicine in pure form for the treatment of sexual dysfunction.

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation, in contact with skin and if swallowed. And it has danger of very serious irreversible effects. During using it, wear suitable protective clothing, gloves and eye/face protection. And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). In addition, you should take off immediately all contaminated clothing.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)[C@@H]5[C@H]4C[C@H]3c2nc1ccccc1c2CCN3C[C@@H]4CC[C@@H]5O
(2)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+/m0/s1
(3)InChIKey: BLGXFZZNTVWLAY-SCYLSFHTBA

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
human	TDLo	oral	643ug/kg/3W-I (0.643mg/kg)	BEHAVIORAL: EXCITEMENT VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Life Sciences. Vol. 30, Pg. 2033, 1982.
man	TDLo	oral	694ug/kg/3D-I (0.694mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION	British Journal of Psychiatry. Vol. 169, Pg. 384, 1996.
mouse	LD50	intraperitoneal	16mg/kg (16mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
mouse	LD50	oral	43mg/kg (43mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
mouse	LD50	subcutaneous	37mg/kg (37mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 5, Pg. 432, 1955.
rabbit	LDLo	intravenous	11mg/kg (11mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1418, 1935.
rabbit	LDLo	subcutaneous	50mg/kg (50mg/kg)		"Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1418, 1935.
women	TDLo	oral	5gm/kg (5000mg/kg)	PERIPHERAL NERVE AND SENSATION: PARESTHESIS BEHAVIORAL: ATAXIA CARDIAC: CHANGE IN RATE	Annals of Emergency Medicine. Vol. 14, Pg. 1002, 1985.

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Standards and Recommendations

Specification