Noribogaine

Noribogaine
Clinical data
Other names	12-Hydroxyibogamine; Ibogamin-12-ol; O-Desmethylibogaine; O-Demethylibogaine; O-Noribogaine; (–)-Noribogaine
Routes of; administration	Oral
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);
Pharmacokinetic data
Elimination half-life	24–50 hours
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;
ChEBI	CHEBI:146264;
ChEMBL	ChEMBL343956;
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 ;
	(verify)

Noribogaine, also known as 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.^[4]^[5]^[6]^[7]

^ ^a ^b Glue P, Lockhart M, Lam F, Hung N, Hung CT, Friedhoff L (February 2015). "Ascending-dose study of noribogaine in healthy volunteers: pharmacokinetics, pharmacodynamics, safety, and tolerability". Journal of Clinical Pharmacology. 55 (2): 189–194. doi:10.1002/jcph.404. PMID 25279818.
^ ^a ^b Glue P, Cape G, Tunnicliff D, Lockhart M, Lam F, Hung N, et al. (November 2016). "Ascending Single-Dose, Double-Blind, Placebo-Controlled Safety Study of Noribogaine in Opioid-Dependent Patients". Clinical Pharmacology in Drug Development. 5 (6): 460–468. doi:10.1002/cpdd.254. PMID 27870477. Visual changes involving change in light perception were reported shortly after dosing, mainly by subjects dosed with 120–180 mg. These changes only occurred during the drug absorption phase, being first reported 1 hour after dosing, and had disappeared by 2.5–3 hours. No hallucinations or dream-like states were reported. In contrast higher ibogaine doses produced symptoms including light sensitivity and closed-eyed dream-like states for 4–8 hours.15
^ Cite error: The named reference Wasko_2018 was invoked but never defined (see the help page).
^ Mash DC, Ameer B, Prou D, Howes JF, Maillet EL (Jul 2016). "Oral noribogaine shows high brain uptake and anti-withdrawal effects not associated with place preference in rodents". Journal of Psychopharmacology. 30 (7). Oxford, England: 688–697. 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): 214–226. 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). Kaunas, Lithuania: 984–988. doi:10.3390/medicina44120123. PMID 19142057.

[Glue_2015-1] Glue P, Lockhart M, Lam F, Hung N, Hung CT, Friedhoff L (February 2015). "Ascending-dose study of noribogaine in healthy volunteers: pharmacokinetics, pharmacodynamics, safety, and tolerability". Journal of Clinical Pharmacology. 55 (2): 189–194. doi:10.1002/jcph.404. PMID 25279818.

[Glue_2016-2] Glue P, Cape G, Tunnicliff D, Lockhart M, Lam F, Hung N, et al. (November 2016). "Ascending Single-Dose, Double-Blind, Placebo-Controlled Safety Study of Noribogaine in Opioid-Dependent Patients". Clinical Pharmacology in Drug Development. 5 (6): 460–468. doi:10.1002/cpdd.254. PMID 27870477. Visual changes involving change in light perception were reported shortly after dosing, mainly by subjects dosed with 120–180 mg. These changes only occurred during the drug absorption phase, being first reported 1 hour after dosing, and had disappeared by 2.5–3 hours. No hallucinations or dream-like states were reported. In contrast higher ibogaine doses produced symptoms including light sensitivity and closed-eyed dream-like states for 4–8 hours.15

[Wasko_2018-3] Cite error: The named reference Wasko_2018 was invoked but never defined (see the help page).

[Mash_2016-4] Mash DC, Ameer B, Prou D, Howes JF, Maillet EL (Jul 2016). "Oral noribogaine shows high brain uptake and anti-withdrawal effects not associated with place preference in rodents". Journal of Psychopharmacology. 30 (7). Oxford, England: 688–697. doi:10.1177/0269881116641331. PMID 27044509. S2CID 40776971.

[Glick_1998-5] Glick SD, Maisonneuve IS (May 1998). "Mechanisms of antiaddictive actions of ibogaine". Annals of the New York Academy of Sciences. 844 (1): 214–226. Bibcode:1998NYASA.844..214G. doi:10.1111/j.1749-6632.1998.tb08237.x. PMID 9668680. S2CID 11416176.

[Baumann_2001-6] 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_2008-7] Kubiliene A, Marksiene R, Kazlauskas S, Sadauskiene I, Razukas A, Ivanov L (2008). "Acute toxicity of ibogaine and noribogaine". Medicina. 44 (12). Kaunas, Lithuania: 984–988. doi:10.3390/medicina44120123. PMID 19142057.

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