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| | IBOGAINE Basic information |
| Product Name: | IBOGAINE | | Synonyms: | 12-methoxy-ibogamin;12-Methoxyibogamine;6,9-Methano-5H-pyrido[1',2':1,2]azepino[4,5-b]indole, ibogamine deriv.;endabuse;Ibogain;Ibogamine, 12-methoxy-;IBOGAINE;Ibogaine solution | | CAS: | 83-74-9 | | MF: | C20H26N2O | | MW: | 310.43 | | EINECS: | 201-498-4 | | Product Categories: | | | Mol File: | 83-74-9.mol |  |
| | IBOGAINE Chemical Properties |
| 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) |
| | IBOGAINE Usage And Synthesis |
| 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is an organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a methoxy group.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)
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| | IBOGAINE Preparation Products And Raw materials |
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