| Identification | Back Directory | [Name]
IBOGAINE | [CAS]
83-74-9 | [Synonyms]
Ibogain
83-74-9
IBOGAINE
endabuse
Ibogaine solution
12-methoxy-ibogamin
12-Methoxyibogamine
Ibogamine, 12-methoxy-
TIANFU CHEM-- IBOGAINE
IbogaineQ: What is
Ibogaine Q: What is the CAS Number of
Ibogaine
6,9-Methano-5H-pyrido[1',2':1,2]azepino[4,5-b]indole, ibogamine deriv. | [EINECS(EC#)]
201-498-4 | [Molecular Formula]
C20H26N2O | [MDL Number]
MFCD03265619 | [MOL File]
83-74-9.mol | [Molecular Weight]
310.43 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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is an organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a methoxy group.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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