Yohimbine hydrochloride
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318989

CAS#: 65-19-0

Description: Yohimbine is an indole alkaloid derived from the bark of the Pausinystalia yohimbe tree in Central Africa. It is a veterinary drug used to reverse sedation in dogs and deer. Yohimbine has been studied as a potential treatment for erectile dysfunction but there is insufficient evidence to rate its effectiveness. Extracts from yohimbe containing yohimbine have been used in traditional medicine in West Africa as an aphrodisiac and have been marketed as dietary supplements.


Price and Availability

Size
Price

1g
USD 150
10g
USD 650
Size
Price

2g
USD 250
20g
USD 950
Size
Price

5g
USD 450

Yohimbine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 318989
Name: Yohimbine hydrochloride
CAS#: 65-19-0
Chemical Formula: C21H27ClN2O3
Exact Mass:
Molecular Weight: 390.908
Elemental Analysis: C, 64.52; H, 6.96; Cl, 9.07; N, 7.17; O, 12.28


Related CAS #: 65-19-0 (HCl)   146-48-5 (free base)    

Synonym: Yohimbine; Yohimbine; Yohimbin; Corynine; Quebrachin; Quebrachine; Yohimex; Yocon; APHRODINE; (+)-Yohimbine; Aphrodyne; ; Aphrosol; Johimbin; Yohimbic acid methyl ester; Actibine; Thybine; Yohimar; Yovital; Yoman; Dayto himbin

IUPAC/Chemical Name: methyl (1R,2S,4aR,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate hydrochloride

InChi Key: PIPZGJSEDRMUAW-VJDCAHTMSA-N

InChi Code: InChI=1S/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

SMILES Code: COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O


Technical Data

Appearance:
White to light yellow solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Dudek M, Knutelska J, Bednarski M, Nowiński L, Zygmunt M, Mordyl B, Głuch-Lutwin M, Kazek G, Sapa J, Pytka K. A Comparison of the Anorectic Effect and Safety of the Alpha2-Adrenoceptor Ligands Guanfacine and Yohimbine in Rats with Diet-Induced Obesity. PLoS One. 2015 Oct 27;10(10):e0141327. doi: 10.1371/journal.pone.0141327. eCollection 2015. PubMed PMID: 26506439; PubMed Central PMCID: PMC4624629.

2: Cohen PA, Wang YH, Maller G, DeSouza R, Khan IA. Pharmaceutical quantities of yohimbine found in dietary supplements in the USA. Drug Test Anal. 2015 Sep 22. doi: 10.1002/dta.1849. [Epub ahead of print] PubMed PMID: 26391406.

3: Zaretsky DV, Zaretskaia MV, DiMicco JA, Rusyniak DE. Yohimbine is a 5-HT1A agonist in rats in doses exceeding 1mg/kg. Neurosci Lett. 2015 Oct 8;606:215-9. doi: 10.1016/j.neulet.2015.09.008. Epub 2015 Sep 12. PubMed PMID: 26366943.

4: Arioli F, Pérez M, Are C, Estarellas C, Luque FJ, Bosch J, Amat M. Stereocontrolled Annulations of Indolo[2,3-a]quinolizidine-Derived Lactams with a Silylated Nazarov Reagent: Access to Allo and Epiallo Yohimbine-Type Derivatives. Chemistry. 2015 Sep 14;21(38):13382-9. doi: 10.1002/chem.201501912. PubMed PMID: 26332232.

5: Chen P, Bryden N. Determination of Yohimbine in Yohimbe Bark and Related Dietary Supplements Using UHPLC-UV/MS: Single-Laboratory Validation. J AOAC Int. 2015 Jul-Aug;98(4):896-901. doi: 10.5740/jaoacint.13-170. PubMed PMID: 26268969.

6: Ball KT, Jarsocrak H, Hyacinthe J, Lambert J, Lockowitz J, Schrock J. Yohimbine reinstates extinguished 3,4-methylenedioxymethamphetamine (MDMA; ecstasy) seeking in rats with prior exposure to chronic yohimbine. Behav Brain Res. 2015 Nov 1;294:1-6. doi: 10.1016/j.bbr.2015.07.056. Epub 2015 Aug 1. PubMed PMID: 26241170; PubMed Central PMCID: PMC4564319.

7: Ball KT, Miller L, Sullivan C, Wells A, Best O, Cavanaugh B, Copus T, Corrigan N, Hawkins S, Kobbe K, Schoener A, Steiger J, Vieweg L. Effects of repeated yohimbine administration on reinstatement of palatable food seeking: involvement of dopamine D(1) -like receptors and food-associated cues. Addict Biol. 2015 Jul 29. doi: 10.1111/adb.12287. [Epub ahead of print] PubMed PMID: 26223161.

8: Prus AJ, Mooney-Leber SM, Berquist MD 2nd, Pehrson AL, Porter NP, Porter JH. The antidepressant drugs fluoxetine and duloxetine produce anxiolytic-like effects in a schedule-induced polydipsia paradigm in rats: enhancement of fluoxetine's effects by the α2 adrenoceptor antagonist yohimbine. Behav Pharmacol. 2015 Aug;26(5):489-94. doi: 10.1097/FBP.0000000000000159. PubMed PMID: 26154437.

9: Feng W, Jiang D, Kee CW, Liu H, Tan CH. Bicyclic Guanidine Catalyzed Asymmetric Tandem Isomerization Intramolecular-Diels-Alder Reaction: The First Catalytic Enantioselective Total Synthesis of (+)-alpha-Yohimbine. Chem Asian J. 2015 Apr 30. doi: 10.1002/asia.201500246. [Epub ahead of print] PubMed PMID: 25932622.

10: Lucas D, Neal-Kababick J, Zweigenbaum J. Characterization and quantitation of yohimbine and its analogs in botanicals and dietary supplements using LC/QTOF-MS and LC/QQQ-MS for determination of the presence of bark extract and yohimbine adulteration. J AOAC Int. 2015 Mar-Apr;98(2):330-5. doi: 10.5740/jaoacint.14-246. PubMed PMID: 25905738.

11: Husain BF, Nanavaty IN, Marathe SV, Rajendran R, Vaidya VA. Hippocampal transcriptional and neurogenic changes evoked by combination yohimbine and imipramine treatment. Prog Neuropsychopharmacol Biol Psychiatry. 2015 Aug 3;61:1-9. doi: 10.1016/j.pnpbp.2015.03.004. Epub 2015 Mar 14. PubMed PMID: 25784603.

12: Nahimi A, Jakobsen S, Munk OL, Vang K, Phan JA, Rodell A, Gjedde A. Mapping α2 adrenoceptors of the human brain with 11C-yohimbine. J Nucl Med. 2015 Mar;56(3):392-8. doi: 10.2967/jnumed.114.145565. Epub 2015 Jan 29. PubMed PMID: 25635132.

13: Steyn LV, Ananthakrishnan K, Anderson MJ, Patek R, Kelly A, Vagner J, Lynch RM, Limesand SW. A Synthetic Heterobivalent Ligand Composed of Glucagon-Like Peptide 1 and Yohimbine Specifically Targets β Cells Within the Pancreas. Mol Imaging Biol. 2015 Aug;17(4):461-70. doi: 10.1007/s11307-014-0817-1. Epub 2015 Jan 21. PubMed PMID: 25604385.

14: Phan JA, Landau AM, Wong DF, Jakobsen S, Nahimi A, Doudet DJ, Gjedde A. Quantification of [(11)C]yohimbine binding to α2 adrenoceptors in rat brain in vivo. J Cereb Blood Flow Metab. 2015 Mar;35(3):501-11. doi: 10.1038/jcbfm.2014.225. Epub 2015 Jan 7. PubMed PMID: 25564241; PubMed Central PMCID: PMC4348393.

15: Nge CE, Gan CY, Lim KH, Ting KN, Low YY, Kam TS. Criofolinine and vernavosine, new pentacyclic indole alkaloids incorporating pyrroloazepine and pyridopyrimidine moieties derived from a common yohimbine precursor. Org Lett. 2014 Dec 19;16(24):6330-3. doi: 10.1021/ol503072g. Epub 2014 Dec 2. PubMed PMID: 25454201.

16: Makau CM, Towett PK, Abelson KS, Kanui TI. Intrathecal administration of clonidine or yohimbine decreases the nociceptive behavior caused by formalin injection in the marsh terrapin (Pelomedusa subrufa). Brain Behav. 2014;4(6):850-7. doi: 10.1002/brb3.287. Epub 2014 Oct 2. PubMed PMID: 25365809; PubMed Central PMCID: PMC4212113.

17: Murahata Y, Miki Y, Hikasa Y. Antagonistic effects of atipamezole, yohimbine, and prazosin on xylazine-induced diuresis in clinically normal cats. Can J Vet Res. 2014 Oct;78(4):304-15. PubMed PMID: 25356000; PubMed Central PMCID: PMC4170770.

18: Chen YW, Fiscella KA, Bacharach SZ, Tanda G, Shaham Y, Calu DJ. Effect of yohimbine on reinstatement of operant responding in rats is dependent on cue contingency but not food reward history. Addict Biol. 2015 Jul;20(4):690-700. doi: 10.1111/adb.12164. Epub 2014 Jul 27. PubMed PMID: 25065697; PubMed Central PMCID: PMC4308573.

19: Corazza O, Martinotti G, Santacroce R, Chillemi E, Di Giannantonio M, Schifano F, Cellek S. Sexual enhancement products for sale online: raising awareness of the psychoactive effects of yohimbine, maca, horny goat weed, and Ginkgo biloba. Biomed Res Int. 2014;2014:841798. doi: 10.1155/2014/841798. Epub 2014 Jun 15. Review. PubMed PMID: 25025070; PubMed Central PMCID: PMC4082836.

20: Li Q, Lin J, Zhang Y, Liu X, Chen XQ, Xu MQ, He L, Li S, Guo N. Differential behavioral responses of zebrafish larvae to yohimbine treatment. Psychopharmacology (Berl). 2015 Jan;232(1):197-208. doi: 10.1007/s00213-014-3656-5. Epub 2014 Jun 25. PubMed PMID: 24958231.