Noribogaine information

Noribogaine
Clinical data
Other names	12-Hydroxyibogamine; Ibogamin-12-ol; O-desmethylibogaine; (-)-Noribogaine;
Legal status
Legal status	AU: S4 (Prescription only); US: Unscheduled (but still a Schedule I analogue due to being a main metabolite of C-I ibogaine);
Identifiers
	IUPAC name (1R,15R,17S,18S)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4(9),5,7-tetraen-7-ol;
CAS Number	481-88-9 ;
PubChem CID	3083548;
ChemSpider	2340735 ;
UNII	87T5QTN9SK;
CompTox Dashboard (EPA)	DTXSID90963998 ;
Chemical and physical data
Formula	C19H24N2O
Molar mass	296.414 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)O;
	InChI InChI=1S/C19H24N2O/c1-2-12-7-11-8-16-18-14(5-6-21(10-11)19(12)16)15-9-13(22)3-4-17(15)20-18/h3-4,9,11-12,16,19-20,22H,2,5-8,10H2,1H3/t11-,12+,16+,19+/m1/s1 ; Key:RAUCDOKTMDOIPF-RYRUWHOVSA-N ;
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Noribogaine (actually O-desmethylibogaine), or 12-hydroxyibogamine, is the principal psychoactive metabolite of the oneirogen ibogaine. It is thought to be involved in the antiaddictive effects of ibogaine-containing plant extracts, such as Tabernanthe iboga.^[1]^[2]^[3]^[4]

^ Mash DC, Ameer B, Prou D, Howes JF, Maillet EL (2016). "Oral noribogaine shows high brain uptake and anti-withdrawal effects not associated with place preference in rodents". J. Psychopharmacol. (Oxford). 30 (7): 688–97. doi:10.1177/0269881116641331. PMID 27044509. S2CID 40776971.
^ Glick SD, Maisonneuve IS (May 1998). "Mechanisms of antiaddictive actions of ibogaine". Annals of the New York Academy of Sciences. 844 (1): 214–26. Bibcode:1998NYASA.844..214G. doi:10.1111/j.1749-6632.1998.tb08237.x. PMID 9668680. S2CID 11416176.
^ Baumann MH, Pablo J, Ali SF, Rothman RB, Mash DC (2001). "Comparative neuropharmacology of ibogaine and its O-desmethyl metabolite, noribogaine". The Alkaloids: Chemistry and Biology. 56: 79–113. doi:10.1016/S0099-9598(01)56009-5. PMID 11705118.
^ Kubiliene A, Marksiene R, Kazlauskas S, Sadauskiene I, Razukas A, Ivanov L (2008). "Acute toxicity of ibogaine and noribogaine". Medicina. 44 (12): 984–8. doi:10.3390/medicina44120123. PMID 19142057.

[pmid27044509-1] Mash DC, Ameer B, Prou D, Howes JF, Maillet EL (2016). "Oral noribogaine shows high brain uptake and anti-withdrawal effects not associated with place preference in rodents". J. Psychopharmacol. (Oxford). 30 (7): 688–97. doi:10.1177/0269881116641331. PMID 27044509. S2CID 40776971.

[pmid9668680-2] Glick SD, Maisonneuve IS (May 1998). "Mechanisms of antiaddictive actions of ibogaine". Annals of the New York Academy of Sciences. 844 (1): 214–26. Bibcode:1998NYASA.844..214G. doi:10.1111/j.1749-6632.1998.tb08237.x. PMID 9668680. S2CID 11416176.

[pmid11705118-3] Baumann MH, Pablo J, Ali SF, Rothman RB, Mash DC (2001). "Comparative neuropharmacology of ibogaine and its O-desmethyl metabolite, noribogaine". The Alkaloids: Chemistry and Biology. 56: 79–113. doi:10.1016/S0099-9598(01)56009-5. PMID 11705118.

[pmid19142057-4] Kubiliene A, Marksiene R, Kazlauskas S, Sadauskiene I, Razukas A, Ivanov L (2008). "Acute toxicity of ibogaine and noribogaine". Medicina. 44 (12): 984–8. doi:10.3390/medicina44120123. PMID 19142057.

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