83-74-9

Usage

Uses

Used in Pharmaceutical Industry:
IBOGAINE is used as a psychoactive substance for its potential applications in treating addiction and substance abuse disorders. It has been reported to have a unique mechanism of action, which involves interacting with various neurotransmitter systems, including serotonin, dopamine, and norepinephrine receptors. This interaction may contribute to its potential therapeutic effects in addiction treatment.
Used in Neuroscientific Research:
IBOGAINE is used as a research tool for studying the neurobiological mechanisms underlying addiction and substance abuse. Its unique pharmacological profile allows researchers to investigate the complex interactions between various neurotransmitter systems and their role in addiction, potentially leading to the development of new therapeutic approaches and interventions.

Purification Methods

Crystallise it from EtOH or aqueous EtOH and sublime it at 150o/0.01mm. It is soluble in organic solvents but insoluble in H2O. The hydrochloride, m 299-300o(dec), is soluble in H2O and alcohols. [Büchi et al. J Am Chem Soc 88 3099 1866, Rosenmund Chem Ber 108 1871 1975, Beilstein 23 III/IV 2742.]

References

Raymond-Hamet., Bull. Soc. Chirn. Fr., 9,620 (1942) Delourme-Houde., Chern. Abstr., 41, 1390 (1947) Bartlett, Dickel, Taylor.,J. Arner. Chern. Soc., 80, 126 (1958) Arai, Coppola, Jeffery., Acta Cryst., 13, 553 (1960) Shamma, Soyster., Experientia, 20,36 (1964) Synthesis: Buchi et ai., f. Arner. Chern. Soc., 88,3099 (1966) Pharmacology: Raymond-Hamet, Rothlin., C.R. Soc. Bioi., 127,592 (1938) Raymond-Hamet, Rothlin., Arch. inst. Pharrnacodyn., 63, 27 (1939) Raymond-Hamet., Cornpt. rend., 201,285 (1940) Raymond-Hamet., C.R. Soc. Bioi., 135, 176 (1941) Raymond-Hamet, Perrot., Bull. Acad. Med., 24,423 (1941) Vincent, Sero., C.R. Soc. Bioi., 136,612 (1942)

InChI:InChI=1/C20H26N2O/c1-3-13-8-12-9-17-19-15(6-7-22(11-12)20(13)17)16-10-14(23-2)4-5-18(16)21-19/h4-5,10,12-13,17,20-21H,3,6-9,11H2,1-2H3/t12-,13+,17+,20+/m1/s1

Synthetic route

voacangine (510-22-5) → ibogaine (83-74-9)

Conditions	Yield
Stage #1: voacangine With potassium hydroxide In ethanol Reflux; Stage #2: With hydrogenchloride In water at 0℃; for 0.0833333h; pH=1; Reflux;	86%
With potassium hydroxide Erwaermen der Reaktionsloesung mit methanol. HCl;

12-methoxy-20,21-didehydro-ibogamine (113950-91-7) → ibogaine (83-74-9)

Conditions	Yield
Hydrogenation;

12-methoxy-ibogamin-19-one (2637-13-0) → ibogaine (83-74-9)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

(17S)-12-methoxy-9,17-dihydro-8,17-cyclo-8,9-seco-ibogamin-9-one → ibogaine (83-74-9)

Conditions	Yield
With lithium aluminium tetrahydride; diethyl ether

ibogaine (83-74-9) → 12-hydroxyibogamine (481-88-9)

Conditions	Yield
With iodine; aluminium In acetonitrile for 3h; Reflux;	76%

tetrahydrofuran (109-99-9) + ibogaine (83-74-9) + iodine (7553-56-2) + NaHCO3 → 12-methoxy-ibogamin-19-one (2637-13-0)

pyridine (110-86-1) + ibogaine (83-74-9) + CrO3 → 12-methoxy-16,17-didehydro-9,17-dihydro-ibogamin-9α-yl hydroperoxide (111066-15-0)

pyridine (110-86-1) + ibogaine (83-74-9) + CrO3 → 12-methoxy-ibogamin-19-one (2637-13-0) + 12-methoxy-ibogamine-8,19-dione (111411-40-6)

chloroform (67-66-3) + ibogaine (83-74-9) + air oxygen → iboluteine + ibochin

Conditions	Yield
Irradiation;

ibogaine (83-74-9) + benzyl chloroformate (501-53-1) → N-CBZ-noribogaine

Conditions	Yield
Stage #1: ibogaine; benzyl chloroformate With N-ethyl-N,N-diisopropylamine at 20℃; Inert atmosphere; Stage #2: With boron tribromide Inert atmosphere;

ibogaine (83-74-9) → ibogaine hydrochloride (5934-55-4)

Conditions	Yield
With hydrogenchloride In diethyl ether

ibogaine (83-74-9) → 12-hydroxyibogamine hydrochloride (110514-35-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminium; iodine / acetonitrile / 3 h / Reflux 2: hydrogenchloride / diethyl ether View Scheme

Upstream product

• 113950-91-7 12-methoxy-20,21-didehydro-ibogamine 
• 2637-13-0 12-methoxy-ibogamin-19-one 
• 510-22-5 voacangine 
• 510-22-5 12-methoxyibogamine-18-carboxylic acid methylester 

Downstream Products

• 481-88-9 12-hydroxyibogamine 
• 5934-55-4 ibogaine hydrochloride 
• 468-11-1 iboluteine 
• 3885-19-6 12-methoxy-16-methyl-ibogamine 
• 1616345-68-6 C₂₈H₃₂N₂O₃ 

Relevant academic research and scientific papers

A Single Administration of the Atypical Psychedelic Ibogaine or Its Metabolite Noribogaine Induces an Antidepressant-Like Effect in Rats

Anecdotal reports and open-label case studies in humans indicated that the psychedelic alkaloid ibogaine exerts profound antiaddictive effects. Ample preclinical evidence demonstrated the efficacy of ibogaine, and its main metabolite, noribogaine, in substance-use-disorder rodent models. In contrast to addiction research, depression-relevant effects of ibogaine or noribogaine in rodents have not been previously examined. We have recently reported that the acute ibogaine administration induced a long-term increase of brain-derived neurotrophic factor mRNA levels in the rat prefrontal cortex, which led us to hypothesize that ibogaine may elicit antidepressant-like effects in rats. Accordingly, we characterized behavioral effects (dose- and time-dependence) induced by the acute ibogaine and noribogaine administration in rats using the forced swim test (FST, 20 and 40 mg/kg i.p., single injection for each dose). We also examined the correlation between plasma and brain concentrations of ibogaine and noribogaine and the elicited behavioral response. We found that ibogaine and noribogaine induced a dose- and time-dependent antidepressant-like effect without significant changes of animal locomotor activity. Noribogaine's FST effect was short-lived (30 min) and correlated with high brain concentrations (estimated >8 μM of free drug), while the ibogaine's antidepressant-like effect was significant at 3 h. At this time point, both ibogaine and noribogaine were present in rat brain at concentrations that cannot produce the same behavioral outcome on their own (ibogaine ～0.5 μM, noribogaine ～2.5 μM). Our data suggests a polypharmacological mechanism underpinning the antidepressant-like effects of ibogaine and noribogaine.

Biosynthesis of an Anti-Addiction Agent from the Iboga Plant

(-)-Ibogaine and (-)-voacangine are plant derived psychoactives that show promise as treatments for opioid addiction. However, these compounds are produced by hard to source plants, making these chemicals difficult for broad-scale use. Here we report the complete biosynthesis of (-)-voacangine, and de-esterified voacangine, which is converted to (-)-ibogaine by heating, enabling biocatalytic production of these compounds. Notably, (-)-ibogaine and (-)-voacangine are of the opposite enantiomeric configuration compared to the other major alkaloids found in this natural product class. Therefore, this discovery provides insight into enantioselective enzymatic formal Diels-Alder reactions.

METHODS AND COMPOSITIONS FOR PREPARING NORIBOGAINE FROM VOACANGINE

Disclosed are methods and compositions for preparing and purifying the non-addictive alkaloid noribogaine.

NORIBOGAINE COMPOSITIONS

Disclosed are noribogaine compositions comprising a very high level of the 2(R), 4(S), 5(S), 6(S) and 18(R) enantiomer and not more than 0.5 wt% of ibogaine relative to the total amount of noribogaine.