Ibogaine HCl

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MedKoo CAT#: 581470

CAS#: 5934-55-4 (HCl)

Description: Ibogaine is one of several indole alkaloids extracted from Tabernanthe iboga, Baill. It has a complex pharmacological profile, and interacts with multiple systems of neurotransmission. Ibogaine has psychoactive properties and appears to modulate tolerance to opiates. Ibogaine HCl is not available (DEA controlled substance).


Price and Availability

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Pricing updated 2020-10-26. Prices are subject to change without notice.

Ibogaine HCl is not available (DEA controlled substance).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 581470
Name: Ibogaine HCl
CAS#: 5934-55-4 (HCl)
Chemical Formula: C20H27ClN2O
Exact Mass: 310.2045
Molecular Weight: 346.899
Elemental Analysis: C, 69.25; H, 7.85; Cl, 10.22; N, 8.08; O, 4.61


Related CAS #: 5934-55-4 (HCl)   83-74-9 (free base)    

Synonym: Ibogaine; Endabuse; Ibogain; (-)-Ibogaine; Ibogaine HCl

IUPAC/Chemical Name: (6R,6aS,7S,9R,11S)-7-ethyl-2-methoxy-6,6a,7,8,9,10,12,13-octahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole hydrochloride

InChi Key: BNDWONRLARSUEV-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H26N2O/c1-3-19-17-10-13-6-4-5-12(22(13)19)9-16-15-11-14(23-2)7-8-18(15)21-20(16)17/h7-8,11-13,17,19,21H,3-6,9-10H2,1-2H3

SMILES Code: COC1=CC2=C(NC3=C2CC[N@@]4[C@]5([H])[C@@]3([H])C[C@@](C4)([H])C[C@@H]5CC)C=C1.[H]Cl


Technical Data

Appearance:
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

Shelf Life:
>3 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).

HS Tariff Code:
2934.99.03.00


References

1: Knuijver T, Belgers M, Markus W, Verkes RJ, van Oosteren T, Schellekens A. Hallucinogen Persisting Perception Disorder After Ibogaine Treatment for Opioid Dependence. J Clin Psychopharmacol. 2018 Oct 8. doi: 10.1097/JCP.0000000000000966. [Epub ahead of print] PubMed PMID: 30300292.

2: Davis AK, Barsuglia JP, Windham-Herman AM, Lynch M, Polanco M. Subjective effectiveness of ibogaine treatment for problematic opioid consumption: Short- and long-term outcomes and current psychological functioning. J Psychedelic Stud. 2017 Nov;1(2):65-73. doi: 10.1556/2054.01.2017.009. Epub 2017 Oct 17. PubMed PMID: 30272050; PubMed Central PMCID: PMC6157925.

3: Wasko MJ, Witt-Enderby PA, Surratt CK. DARK Classics in Chemical Neuroscience: Ibogaine. ACS Chem Neurosci. 2018 Oct 9. doi: 10.1021/acschemneuro.8b00294. [Epub ahead of print] PubMed PMID: 30216039.

4: Steinberg C, Deyell MW. Cardiac arrest after ibogaine intoxication. J Arrhythm. 2018 Jun 12;34(4):455-457. doi: 10.1002/joa3.12061. eCollection 2018 Aug. PubMed PMID: 30167018; PubMed Central PMCID: PMC6111465.

5: Devault DA, Maguet H, Merle S, Péné-Annette A, Lévi Y. Wastewater-based epidemiology in low Human Development Index states: bias in consumption monitoring of illicit drugs. Environ Sci Pollut Res Int. 2018 Oct;25(28):27819-27838. doi: 10.1007/s11356-018-2864-7. Epub 2018 Aug 14. PubMed PMID: 30109683.

6: Farrow SC, Kamileen MO, Meades J, Ameyaw B, Xiao Y, O'Connor SE. Cytochrome P450 and O-methyltransferase catalyze the final steps in the biosynthesis of the anti-addictive alkaloid ibogaine from Tabernanthe iboga. J Biol Chem. 2018 Sep 7;293(36):13821-13833. doi: 10.1074/jbc.RA118.004060. Epub 2018 Jul 20. PubMed PMID: 30030374; PubMed Central PMCID: PMC6130943.

7: Schenberg EE. Psychedelic-Assisted Psychotherapy: A Paradigm Shift in Psychiatric Research and Development. Front Pharmacol. 2018 Jul 5;9:733. doi: 10.3389/fphar.2018.00733. eCollection 2018. PubMed PMID: 30026698; PubMed Central PMCID: PMC6041963.

8: Davis AK, Renn E, Windham-Herman AM, Polanco M, Barsuglia JP. A Mixed-Method Analysis of Persisting Effects Associated with Positive Outcomes Following Ibogaine Detoxification. J Psychoactive Drugs. 2018 Jul 18:1-11. doi: 10.1080/02791072.2018.1487607. [Epub ahead of print] PubMed PMID: 30020025.

9: Yu HF, Qin XJ, Ding CF, Wei X, Yang J, Luo JR, Liu L, Khan A, Zhang LC, Xia CF, Luo XD. Nepenthe-Like Indole Alkaloids with Antimicrobial Activity from Ervatamia chinensis. Org Lett. 2018 Jul 6;20(13):4116-4120. doi: 10.1021/acs.orglett.8b01675. Epub 2018 Jun 21. PubMed PMID: 29927253.

10: Mash DC, Duque L, Page B, Allen-Ferdinand K. Ibogaine Detoxification Transitions Opioid and Cocaine Abusers Between Dependence and Abstinence: Clinical Observations and Treatment Outcomes. Front Pharmacol. 2018 Jun 5;9:529. doi: 10.3389/fphar.2018.00529. eCollection 2018. PubMed PMID: 29922156; PubMed Central PMCID: PMC5996271.

11: González J, Prieto JP, Rodríguez P, Cavelli M, Benedetto L, Mondino A, Pazos M, Seoane G, Carrera I, Scorza C, Torterolo P. Ibogaine Acute Administration in Rats Promotes Wakefulness, Long-Lasting REM Sleep Suppression, and a Distinctive Motor Profile. Front Pharmacol. 2018 Apr 27;9:374. doi: 10.3389/fphar.2018.00374. eCollection 2018. PubMed PMID: 29755349; PubMed Central PMCID: PMC5934978.

12: Malcolm BJ, Polanco M, Barsuglia JP. Changes in Withdrawal and Craving Scores in Participants Undergoing Opioid Detoxification Utilizing Ibogaine. J Psychoactive Drugs. 2018 Jul-Aug;50(3):256-265. doi: 10.1080/02791072.2018.1447175. Epub 2018 Apr 2. PubMed PMID: 29608409.

13: Oreščanin-Dušić Z, Tatalović N, Vidonja-Uzelac T, Nestorov J, Nikolić-Kokić A, Mijušković A, Spasić M, Paškulin R, Bresjanac M, Blagojević D. The Effects of Ibogaine on Uterine Smooth Muscle Contractions: Relation to the Activity of Antioxidant Enzymes. Oxid Med Cell Longev. 2018 Feb 11;2018:5969486. doi: 10.1155/2018/5969486. eCollection 2018. PubMed PMID: 29599898; PubMed Central PMCID: PMC5828116.

14: C Mash D. Breaking the cycle of opioid use disorder with Ibogaine. Am J Drug Alcohol Abuse. 2018;44(1):1-3. doi: 10.1080/00952990.2017.1357184. Epub 2017 Dec 7. PubMed PMID: 29215917.

15: Freissmuth M, Stockner T, Sucic S. SLC6 Transporter Folding Diseases and Pharmacochaperoning. Handb Exp Pharmacol. 2018;245:249-270. doi: 10.1007/164_2017_71. Review. PubMed PMID: 29086036.

16: Arias HR, Jin X, Feuerbach D, Drenan RM. Selectivity of coronaridine congeners at nicotinic acetylcholine receptors and inhibitory activity on mouse medial habenula. Int J Biochem Cell Biol. 2017 Nov;92:202-209. doi: 10.1016/j.biocel.2017.10.006. Epub 2017 Oct 16. PubMed PMID: 29042244; PubMed Central PMCID: PMC5903430.

17: Asjad HMM, Kasture A, El-Kasaby A, Sackel M, Hummel T, Freissmuth M, Sucic S. Pharmacochaperoning in a Drosophila model system rescues human dopamine transporter variants associated with infantile/juvenile parkinsonism. J Biol Chem. 2017 Nov 24;292(47):19250-19265. doi: 10.1074/jbc.M117.797092. Epub 2017 Sep 29. PubMed PMID: 28972153; PubMed Central PMCID: PMC5702666.

18: Yip L, Deng JF. On the relationship between ibogaine and noribogaine. Clin Toxicol (Phila). 2018 Jan;56(1):77. doi: 10.1080/15563650.2017.1339890. Epub 2017 Jul 6. PubMed PMID: 28681614.

19: Brown TK, Alper K. Treatment of opioid use disorder with ibogaine: detoxification and drug use outcomes. Am J Drug Alcohol Abuse. 2018;44(1):24-36. doi: 10.1080/00952990.2017.1320802. Epub 2017 May 25. PubMed PMID: 28541119.

20: Henstra M, Wong L, Chahbouni A, Swart N, Allaart C, Sombogaard F. Toxicokinetics of ibogaine and noribogaine in a patient with prolonged multiple cardiac arrhythmias after ingestion of internet purchased ibogaine. Clin Toxicol (Phila). 2017 Jul;55(6):600-602. doi: 10.1080/15563650.2017.1287372. Epub 2017 Feb 9. PubMed PMID: 28489458.