Principal psychoactive metabolite of the oneirogen ibogaine
Pharmaceutical compound
Noribogaine Other names 12-Hydroxyibogamine; Ibogamin-12-ol; O-desmethylibogaine; (-)-Noribogaine; Legal status
AU : S4 (Prescription only)
US : Unscheduled (but still a Schedule I analogue due to being a main metabolite of C-I ibogaine )
(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 PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) Formula C 19 H 24 N 2 O Molar mass 296.414 g·mol−1 3D model (JSmol )
CC[C@H]1C[C@@H]2C[C@@H]3[C@H]1N(C2)CCC4=C3NC5=C4C=C(C=C5)O
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
Y Key:RAUCDOKTMDOIPF-RYRUWHOVSA-N
Y
N Y (what is this?) (verify)
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]
Pharmacology
Noribogaine is a potent serotonin reuptake inhibitor ,[ 5] but does not affect the reuptake of dopamine .[ 6] Unlike ibogaine, noribogaine does not bind to the sigma-2 receptor .[ 7] [ 8] Similarly to ibogaine, noribogaine acts as a weak NMDA receptor antagonist and binds to opioid receptors .[ 9] It has greater affinity for each of the opioid receptors than does ibogaine.[ 10]
Noribogaine is a hERG inhibitor and appears at least as potent as ibogaine.[ 11] The inhibition of the hERG potassium channel delays the repolarization of cardiac action potentials , resulting in QT interval prolongation and, subsequently, in arrhythmias and sudden cardiac arrest .[ 12]
κ-Opioid receptor
Noribogaine has been determined to act as a biased agonist of the κ-opioid receptor (KOR).[ 13] It activates the G protein (GDP-GTP exchange) signaling pathway with 75% the efficacy of dynorphin A (EC50 = 9 μM), but it is only 12% as efficacious at activating the β-arrestin pathway.[ 13] With an IC50 value of 1 μM, it can be regarded as an antagonist of the latter pathway.[ 13]
The β-arrestin signaling pathway is hypothesized to be responsible for the anxiogenic , dysphoric , or anhedonic effects of KOR activation.[ 14] Attenuation of the β-arrestin pathway by noribogaine may be the reason for the absence of these aversive effects,[ 13] while retaining analgesic and antiaddictive properties. This biased KOR activity makes it stand out from the other iboga alkaloids like ibogaine and the derivative 18-methoxycoronaridine (18-MC).[ 13]
Benzofuran analog
In 2024, a synthetic benzofuran analog (oxa-noribogaine) was reported that is devoid of the pro-arrhythmic side effect. It has analgesic effects as a potent (atypical) kappa-opioid receptor partial agonist and, opposed to standard KOR agonists, is characterized by the absence of pro-depressant effects. It induces a robust KOR-dependent increase in GDNF protein levels in the ventral tegmental area and medial prefrontal cortex . After a single dose or short-term treatment, oxa-noribogaine induces long-lasting suppression of opioid drug seeking in rodent relapse models. It also counteracts persistent opioid-induced hyperalgesia .[ 15]
See also
References
^ 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 .
^ Max M. Houck (26 January 2015). Forensic Chemistry . Elsevier Science. pp. 164–. ISBN 978-0-12-800624-5 .
^ Baumann MH, Rothman RB, Pablo JP, Mash DC (May 2001). "In vivo neurobiological effects of ibogaine and its O-desmethyl metabolite, 12-hydroxyibogamine (noribogaine), in rats" . The Journal of Pharmacology and Experimental Therapeutics . 297 (2): 531–539. PMID 11303040 .
^ Paul Gahlinger (30 December 2003). Illegal Drugs . Penguin Publishing Group. pp. 304–. ISBN 978-1-4406-5024-6 .
^ Alper KR, Glick SD (2001). Ibogaine: Proceedings from the First International Conference . Gulf Professional Publishing. pp. 107–. ISBN 978-0-12-053206-3 .
^ Donald G. Barceloux (20 March 2012). Medical Toxicology of Drug Abuse: Synthesized Chemicals and Psychoactive Plants . John Wiley & Sons. pp. 869–. ISBN 978-0-471-72760-6 .
^ Pearl SM, Herrick-Davis K, Teitler M, Glick SD (March 1995). "Radioligand-binding study of noribogaine, a likely metabolite of ibogaine". Brain Research . 675 (1–2): 342–344. doi :10.1016/0006-8993(95)00123-8 . PMID 7796150 . S2CID 28001919 .
^ Alper K, Bai R, Liu N, Fowler SJ, Huang XP, Priori SG, Ruan Y (2016). "hERG Blockade by Iboga Alkaloids" . Cardiovasc. Toxicol . 16 (1): 14–22. doi :10.1007/s12012-015-9311-5 . PMID 25636206 . S2CID 16071274 .
^ Litjens RP, Brunt TM (2016). "How toxic is ibogaine?". Clin Toxicol . 54 (4): 297–302. doi :10.3109/15563650.2016.1138226 . PMID 26807959 . S2CID 7026570 .
^ a b c d e Maillet EL, Milon N, Heghinian MD, Fishback J, Schürer SC, Garamszegi N, Mash DC (2015). "Noribogaine is a G-protein biased κ-opioid receptor agonist" . Neuropharmacology . 99 : 675–88. doi :10.1016/j.neuropharm.2015.08.032 . PMID 26302653 .
^ Ehrich JM, Messinger DI, Knakal CR, Kuhar JR, Schattauer SS, Bruchas MR, Zweifel LS, Kieffer BL, Phillips PE, Chavkin C (2015). "Kappa Opioid Receptor-Induced Aversion Requires p38 MAPK Activation in VTA Dopamine Neurons" . J. Neurosci . 35 (37): 12917–31. doi :10.1523/JNEUROSCI.2444-15.2015 . PMC 4571610 . PMID 26377476 .
^ Havel V, Kruegel AC, Bechand B, et al. (2024). "Oxa-Iboga alkaloids lack cardiac risk and disrupt opioid use in animal models" . Nat Commun . 15 (1): 8118. Bibcode :2024NatCo..15.8118H . doi :10.1038/s41467-024-51856-y . PMC 11415492 . PMID 39304653 .
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Antagonists: Atypical antipsychotics (e.g., iloperidone , risperidone , sertindole )
AV965
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Agonists: Anpirtoline
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Agonists: CP-122,288
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GR-46611
L-694247
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PNU-109291
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Serotonin (5-HT)
TGBA01AD
Triptans (e.g., almotriptan , avitriptan , donitriptan , eletriptan , frovatriptan , naratriptan , rizatriptan , sumatriptan , zolmitriptan )
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Agonists: 25H/NB series (e.g., 25I-NBF , 25I-NBMD , 25I-NBOH , 25I-NBOMe , 25B-NBOMe , 25C-NBOMe , 25TFM-NBOMe , 2CBCB-NBOMe , 25CN-NBOH , 2CBFly-NBOMe )
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2C-B-FLY
2CB-Ind
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α-Alkyltryptamines (e.g., 5-Cl-αMT , 5-Fl-αMT , 5-MeO-αET , 5-MeO-αMT , α-Me-5-HT , αET , αMT )
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Antagonists: 5-I-R91150
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AC-90179
Adatanserin
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AMDA
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SR-46349B
TGBA01AD
Teniloxazine
Temanogrel
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
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Agonists: 4-Methylaminorex
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BW-723C86
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PNU-22394
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Serotonin (5-HT)
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Antagonists: Agomelatine
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Cyproheptadine
EGIS-7625
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Ketanserin
LY-393558
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SB-206553
SB-215505
SB-221284
SB-228357
SDZ SER-082
Tegaserod
Tetracyclic antidepressants (e.g., amoxapine , mianserin , mirtazapine )
Trazodone
Typical antipsychotics (e.g., chlorpromazine )
TIK-301
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A-372159
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Alstonine
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Dimemebfe
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Flumexadol
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MK-212
ORG-12962
ORG-37684
Oxaflozane
PHA-57378
Phenethylamines (e.g., lophophine , mescaline )
Piperazines (e.g., aripiprazole , BZP , mCPP , quipazine , TFMPP )
PNU-22394
PNU-181731
Ro60-0175
Ro60-0213
Serotonin (5-HT)
Tryptamines (e.g., 5-BT , 5-CT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
Vabicaserin
WAY-629
WAY-161503
YM-348
Antagonists: Adatanserin
Agomelatine
Atypical antipsychotics (e.g., asenapine , clorotepine , clozapine , fluperlapine , iloperidone , melperone , olanzapine , paliperidone , quetiapine , risperidone , sertindole , ziprasidone , zotepine )
Captodiame
CEPC
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Cyproheptadine
Deramciclane
Desmetramadol
Dotarizine
Eltoprazine
Ergolines (e.g., amesergide , bromocriptine , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
Etoperidone
Fluoxetine
FR-260010
Irindalone
Ketanserin
Ketotifen
Latrepirdine (dimebolin)
Medifoxamine
Metitepine (methiothepin)
Nefazodone
Pirenperone
Pizotifen
Propranolol
Ritanserin
RS-102221
S-14671
SB-200646
SB-206553
SB-221284
SB-228357
SB-242084
SB-243213
SDZ SER-082
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
TIK-301
Tramadol
Trazodone
Tricyclic antidepressants (e.g., amitriptyline , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine , pimozide , pipamperone , thioridazine )
Xylamidine
5-HT3 –7
5-HT3
Agonists: Alcohols (e.g., butanol , ethanol (alcohol) , trichloroethanol )
m-CPBG
Phenylbiguanide
Piperazines (e.g., BZP , mCPP , quipazine )
RS-56812
Serotonin (5-HT)
SR-57227
SR-57227A
Tryptamines (e.g., 2-Me-5-HT , 5-CT , bufotenidine (5-HTQ) )
Volatiles/gases (e.g., halothane , isoflurane , toluene , trichloroethane )
YM-31636
Antagonists: Alosetron
Anpirtoline
Arazasetron
AS-8112
Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine )
Azasetron
Batanopride
Bemesetron (MDL-72222)
Bupropion
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
Hydroxybupropion
Lerisetron
Memantine
Ondansetron
Palonosetron
Ramosetron
Renzapride
Ricasetron
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine , mianserin , mirtazapine )
Thujone
Tropanserin
Tropisetron
Typical antipsychotics (e.g., loxapine )
Volatiles/gases (e.g., nitrous oxide , sevoflurane , xenon )
Vortioxetine
Zacopride
Zatosetron
5-HT4
5-HT5A
5-HT6
Agonists: Ergolines (e.g., dihydroergocryptine , dihydroergotamine , ergotamine , lisuride , LSD , mesulergine , metergoline , methysergide )
Hypidone
Serotonin (5-HT)
Tryptamines (e.g., 2-Me-5-HT , 5-BT , 5-CT , 5-MT , Bufotenin , E-6801 , E-6837 , EMD-386088 , EMDT , LY-586713 , N-Me-5-HT , ST-1936 , tryptamine )
WAY-181187
WAY-208466
Antagonists: ABT-354
Atypical antipsychotics (e.g., aripiprazole , asenapine , clorotepine , clozapine , fluperlapine , iloperidone , olanzapine , tiospirone )
AVN-101
AVN-211
AVN-322
AVN-397
BGC20-760
BVT-5182
BVT-74316
Cerlapirdine
EGIS-12,233
GW-742457
Idalopirdine
Ketanserin
Landipirdine
Latrepirdine (dimebolin)
Masupirdine
Metitepine (methiothepin)
MS-245
PRX-07034
Ritanserin
Ro 04-6790
Ro 63-0563
SB-258585
SB-271046
SB-357134
SB-399885
SB-742457
Tetracyclic antidepressants (e.g., amoxapine , mianserin )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , doxepin , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine )
5-HT7
Antagonists: Atypical antipsychotics (e.g., amisulpride , aripiprazole , asenapine , brexpiprazole , clorotepine , clozapine , fluperlapine , olanzapine , risperidone , sertindole , tiospirone , ziprasidone , zotepine )
Butaclamol
DR-4485
EGIS-12,233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215,840
Metitepine (methiothepin)
Ritanserin
SB-258719
SB-258741
SB-269970
SB-656104
SB-656104A
SB-691673
SLV-313
SLV-314
Spiperone
SSR-181507
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )
Tricyclic antidepressants (e.g., amitriptyline , clomipramine , imipramine )
Typical antipsychotics (e.g., acetophenazine , chlorpromazine , chlorprothixene , fluphenazine , loxapine , pimozide )
Vortioxetine
Tryptamines
1-Methyl-T
1-Methylpsilocin
2-HO-NMT
2-Me-DET
2-Methyl-5-HT
2,N ,N -TMT
4,5-DHP-DMT
4-AcO-DALT
4-AcO-DET
4-AcO-DiPT
4-AcO-DPT
4-AcO-EPT
4-AcO-MALT
4-AcO-MET
4-AcO-MiPT
4-AcO-NMT
4-AcO-TMT
4-F-5-MeO-DMT
4-Fluoro-T
4-HO-5-MeO-DMT
4-HO-DALT
4-HO-DBT
4-HO-DET
4-HO-DiPT
4-HO-DPT
4-HO-DSBT
4-HO-EPT
4-HO-MALT
4-HO-MET
4-HO-McPT
4-HO-McPeT
4-HO-MiPT
4-HO-MPT
4-HO-MsBT
4-HO-NALT
4-HO-NMT
4-HO-PiPT
4-HO-pyr-T
4-HO-TMT
4-HT
4-MeO-DiPT
4-MeO-DMT
4-MeO-MiPT
4-MeO-T
4-PrO-DMT
4,5-MDO-DMT
4,5-MDO-DiPT
5-BT
5-Bromo-DMT
5-Bromo-T
5-Chloro-DMT
5-Chloro-T
5-CT
5-Ethoxy-DMT
5-Ethyl-DMT
5-Fluoro-DET
5-Fluoro-DMT
5-Fluoro-EPT
5-Fluoro-MET
5-Fluoro-T
5-HO-DiPT
5-HTP (oxitriptan)
5-MeO-2-TMT
5-MeO-34MPEMT
5-MeO-7,N ,N -TMT
5-MeO-DALT
5-MeO-DBT
5-MeO-DET
5-MeO-DiPT
5-MeO-DMT
5-MeO-DPT
5-MeO-EiPT
5-MeO-EPT
5-MeO-MALT
5-MeO-MET
5-MeO-MiPT
5-MeO-NET
5-MeO-NiPT
5-MeO-NMT
5-MeO-pyr-T
5-MeO-NBpBrT
5-MeO-T (5-MT; mexamine)
5-MeO-T-NBOMe
5-MeS-DMT
5-Methyl-DMT
5-Methyl-T
5-MT-NB3OMe
5-NOT
5,6-MeO-MiPT
5,6-MDO-DiPT
5,6-MDO-DMT
5,6-MDO-MiPT
5,6-DHT
5,7-DHT
6-Fluoro-DMT
6-Fluoro-T
6-MeO-DMT
6-MeO-T
6-Methyl-T
7-Chloro-T
7-MeO-T
7-Methyl-DMT
7-Methyl-T
Acetryptine (5-AT)
Aeruginascin (4-PO-TMT)
AGH-107
AGH-192
AH-494
ALiPT
Alpertine
Baeocystin (4-PO-NMT)
Benzotript (4-chlorobenzoyl-L -tryptophan)
Bufotenidine (5-HTQ)
Bufotenin (5-HO-DMT)
Convolutindole A
CP-132,484
DALT
DBT
Desformylflustrabromine
DET
DiPT
DMT
DPT
E-6801
E-6837
EiPT
EMDT
EPT
Ethocybin (4-PO-DET)
FGIN-127
FGIN-143
FT-104
HIOC
Idalopirdine
Indolylethylfentanyl
Indorenate
Iprocin (4-HO-DiPT)
Isamide
Lespedamine
MBT
MET
Milipertine
Miprocin (4-HO-MiPT)
MiPT
MPT
MS-245
MSBT
N -Feruloylserotonin (moschamine)
NET/NETP
NiPT
NMT
Norbaeocystin (4-PO-T)
NTBT
O-4310
O -Pivalylbufotenine
Oxypertine
PiPT
Psilacetin (O -acetylpsilocin; 4-AcO-DMT)
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Pyr-T
RS134-49
Serotonin (5-HT)
Solypertine
ST-1936
Tryptamine (T)
Tryptophan
Yuremamine
Z2876442907
N -Acetyltryptaminesα-Alkyltryptamines
2,α-DMT
4-HO-αMT
4-HO-MPMI (lucigenol)
4-Me-αET
4-Me-αMT
5-Chloro-αET
5-Chloro-αMT
5-Ethoxy-αMT
5-Fluoro-αET
5-Fluoro-αMT
5-iPrO-αMT
5-MeO-α,N ,N -TMT
5-MeO-αET
5-MeO-αMT
5-MeO-MPMI
5-Methyl-αET
6-Fluoro-αMT
7-Chloro-αMT
7-Methyl-αET
α-Methyl-5-HTP
α-Methylmelatonin
α-Methylserotonin (5-HO-αMT)
α-Methyltryptophan (αMTP)
α,N -DMT (N -methyl-αMT)
α,N ,N -TMT
α,N ,O -TMS
αET (etryptamine)
αMT
AL-37350A (4,5-DHP-αMT)
BK-5Br-NM-AMT
BK-5Cl-NM-AMT
BK-5F-NM-AMT
BK-NM-AMT
BNC-210
BW-723C86
CP-135807
IPAP (α,N -DPT)
MPMI
Triptans Cyclized tryptamines
Bay R 1531
Ciclindole
Cyclic 3-OHM
Ergolines and lysergamides (e.g., LSD )
Flucindole
Harmala alkaloids and β-carbolines (e.g., 6-MeO-THH , 9-Me-BC , β-carboline (norharman) , harmaline , harmalol , harmane , harmine , pinoline , tetrahydroharmine , tryptoline )
Iboga alkaloids and related (e.g., DM-506 (ibogaminalog) , ibogaine , ibogamine , noribogaine , tabernanthalog , tabernanthine )
LY-266,097
Metralindole
NDTDI
PHA-57378
PNU-22394
PNU-181731
RU-28306
Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine )
Isotryptamines Related compounds