IBOGAINE Property

Melting point:

152-153°

alpha 

D20 -53° (in 95% ethanol)

Boiling point:

450.59°C (rough estimate)

Density 

1.0633 (rough estimate)

refractive index 

1.6800 (estimate)

storage temp. 

2-8°C

pka

8.1 in 80% methylcellosolve

EPA Substance Registry System

Ibogaine (83-74-9)

Safety

Hazard Codes 

F,T

Risk Statements 

11-23/24/25-39/23/24/25

Safety Statements 

7-16-36/37-45

RIDADR 

1544

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

83-74-9(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

IBOGAINE Chemical Properties,Usage,Production

Description

This indole alkaloid occurs in the root of Tabernanthe iboga Baill. It was first examined in detail by Raymond-Hamet who assigned to it the empirical formula C19H24(26)ON2, now altered to that given above. The base forms colourless crystals from EtOH and is laevorotatory with [Q1D - 53° (EtOH). It is insoluble in Et20, slightly so in Me2CO or CHC1 3 but dissolves freely in MeOH, EtOH or H20. The alkaloid yields a hydrochloride, m.p. 299°C (dec.); lQlhs - 67° (MeOH) or - 37.3° (H20). It contains one methoxyl group and gives the typical indole reactions. On distillation with Zn dust or soda-lime it furnishes products which are indole derivatives with the ~-position free.
In a manner similar to that of cocaine, the alkaloid potentiates the pressor action of adrenaline and abolishes the sino-carotid reflexes. Unlike cocaine, however, it also augments the action of tyramine and that of dl-ephedrine to a slight extent. Vincent and Sero have reported that it inhibits the action of serum cholinesterase.

Definition

ChEBI: Ibogaine is an organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a methoxy group. It has a role as a plant metabolite, an inhibitor, a hallucinogen and a oneirogen. It is a monoterpenoid indole alkaloid, an organic heteropentacyclic compound and an aromatic ether. It is functionally related to an ibogamine. It is a conjugate base of an ibogaine(1+).

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)