12-Methoxyibogamin

Bezeichnung:12-Methoxyibogamin

CAS-Nr83-74-9

Englisch Name:IBOGAINE

CBNumberCB9300459

SummenformelC20H26N2O

Molgewicht310.43

MOL-Datei83-74-9.mol

Synonyma

12-Methoxyibogamin

12-Methoxyibogamin physikalisch-chemischer Eigenschaften

Schmelzpunkt	152-153°
alpha	D20 -53° (in 95% ethanol)
Siedepunkt	450.59°C (rough estimate)
Dichte	1.0633 (rough estimate)
Brechungsindex	1.6800 (estimate)
storage temp.	2-8°C
pka	8.1 in 80% methylcellosolve
EPA chemische Informationen	Ibogaine (83-74-9)

Sicherheit

Kennzeichnung gefährlicher	F,T
R-Sätze:	11-23/24/25-39/23/24/25
S-Sätze:	7-16-36/37-45
RIDADR	1544
HazardClass	6.1(b)
PackingGroup	III
Giftige Stoffe Daten	83-74-9(Hazardous Substances Data)

Gefahreninformationscode (GHS)

IBOGAINE Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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is an organic heteropentacyclic compound that is ibogamine in which the indole hydrogen para to the indole nitrogen has been replaced by a methoxy group.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+).
läuterung methode
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.]
Einzelnachweise
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)

12-Methoxyibogamin Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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