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Pharmaceutical compound
Fenharmane Other names Fenharman; Phenharman; Phenharmane; Fenoharman; Fenoharmane; Phenoharman; Phenoharmane; 1-Benzyl-1,2,3,4-tetrahydronorharmane; Benzyltetrahydronorharman Drug class Sedative ; Tranquilizer ; Reserpine-like agent
1-benzyl-2,3,4,9-tetrahydro-1H -pyrido[3,4-b]indole
CAS Number PubChem CID ChemSpider UNII ChEMBL Formula C 18 H 18 N 2 Molar mass −1 3D model (JSmol )
C1CNC(C2=C1C3=CC=CC=C3N2)CC4=CC=CC=C4
InChI=1S/C18H18N2/c1-2-6-13(7-3-1)12-17-18-15(10-11-19-17)14-8-4-5-9-16(14)20-18/h1-9,17,19-20H,10-12H2
Key:LHVNPTMRAQQPID-UHFFFAOYSA-N
Fenharmane (INN Tooltip International Nonproprietary Name ), also known as 1-benzyl-1,2,3,4-tetrahydronorharmane , is a sedative and tranquilizer of the β-carboline family.[ 1] [ 2] reserpine , a monoamine-depleting agent .[ 3] [ 4] [ 5] [ 6] depression analogously to reserpine.[ 7] [ 8] Czechoslovakia in the late 1950s.[ 3] [ 2] [ 9]
^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies 144– 145. ISBN 978-1-4757-2085-3 ^ a b Švestka J (2000). "S31.03 The history of czech psychopharmacology and psychopharmacotherapy of affective and schizophrenic disorders" (PDF) . European Psychiatry . 15 (S2): 277s – 277s . doi :10.1016/S0924-9338(00)94205-6 ISSN 0924-9338 . Retrieved 30 May 2025 . ^ a b Dlabac A, Macek K, Vanecek M, Trcka V (April 1959). "Reserpinový úćinek fenoharmanu" [Reserpine-like action of phenoharmane]. Ceskoslovenska Fysiologie (in Czech). 8 (3): 177– 178. PMID 13671512 . ^ Trcka V, Dlabac A, Vanecek M (1961). "[The reserpine-like action of 1-benzyl-1,2,3,4-tetrahydronorharmane (fenoharman)]". Journal de Physiologie (in French). 53 : 488– 489. PMID 13777950 . ^ Nahunek K, Rodova A, Hosak L, Jaros M, Hadlik J (July 1962). "[Nialamid and its combinations with reserpine-like substances (fenoharman, reserpine) in the therapy of endogenous depressions]". Deutsches Medizinisches Journal (in German). 13 : 424– 425. PMID 14477998 . ^ Rysanek K, Vitek V, Spankova H (1962). "[Comparative effects of Reserpine and Fenoharman on the absorption and liberation of serotonin in vivo and in vitro]". Activitas Nervosa Superior (in Czech). 4 : 220– 221. PMID 14495652 . ^ Bermanzohn PC, Siris SG (1992). "Akinesia: a syndrome common to parkinsonism, retarded depression, and negative symptoms of schizophrenia". Comprehensive Psychiatry . 33 (4): 221– 232. doi :10.1016/0010-440x(92)90045-r . PMID 1353715 . ^ Tesařová O (1972). "Experimental Depression Caused by Apomorphine and Phenoharmane" . Pharmacopsychiatry . 5 (01): 13– 19. doi :10.1055/s-0028-1094329 . ISSN 0176-3679 . Retrieved 30 May 2025 . ^ Vinar O (November 1960). "[Use of Fenoharman, a new Czechoslovakian preparation, in psychiatry (preliminary communication)]". Casopis Lekaru Ceskych (in Czech). 99 : 1422– 1424. PMID 13781443 .
Tryptamines 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines
2-Methyl-5-HT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DiPT 5-HO-NiPT 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 (N ,N ,O -TMS; O -methylbufotenine) 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 (O ,N -DMS) 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine; O -methylserotonin) 5-MeO-T-NBOMe 5-MT-NB3OMe 5-NOT 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ; N ,N ,N -TMS) Bufotenin (5-HO-DMT; N ,N -DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)Norbufotenin (5-HO-NMT; NMS) O -Acetylbufotenine (5-AcO-DMT)O -Pivalylbufotenine (5-(t -BuCO)-DMT)Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT) N -Acetyltryptaminesα-Alkyltryptamines
5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O -DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 Triptans Cyclized tryptamines
Barettin Bufothionine Ciclindole Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD )Flucindole Frovatriptan Harmala alkaloidsβ-carbolines (e.g., 6-MeO-THH , 9-Me-BC , β-carboline (norharman) , fenharmane , harmaline , harmalol , harmane , harmine , pinoline , tetrahydroharmine , tryptoline )Iboga alkaloidsibogaine , ibogamine , noribogaine , tabernanthine )Ibogalogs (e.g., fluorogainalog , ibogainalog , ibogaminalog (DM-506) , LS-22925 , noribogainalog , noribogaminalog , PNU-22394 , tabernanthalog )Imidazolylindoles (e.g., AGH-107 , AGH-192 , AH-494 )LY-266,097 LY-344864 Metralindole O -MethylnordehydrobufoteninePartial ergolines and lysergamides (e.g., NDTDI , RU-27849 , RU-28251 , RU-28306 , LY-178210 , Bay R 1531 (LY-197206) , LY-293284 , 10,11-seco-LSD , 10,11-secoergoline (α,N -Pip-T) , CT-5252 )Pertines (e.g., alpertine , milipertine , oxypertine , solypertine )PHA-57378 Piperidinylethylindoles (e.g., Pip-T , indolylethylfentanyl )Pyrrolidinylethylindoles (e.g., Pyr-T , 4-HO-pyr-T , 5-MeO-pyr-T , 4-F-5-MeO-pyr-T )Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5F-MPMI , 5-MeO-MPMI , CP-135807 , eletriptan )Tetrahydropyridinylindoles (e.g., RS134-49 , RU-28253 )Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine ) Isotryptamines Related compounds
2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT Amedalin Benzindopyrine Benzofurans (e.g., 3-APB , 5-MeO-DiBF , BPAP , 3-F-BPAP , dimemebfe , mebfap )Benzothiophenes (e.g., 3-APBT )CP-94253 CT-4436 Daledalin Gramine Histamine I-32 IAL IN-399 Indazoles (e.g., AL-34662 , AL-38022A , O -methyl-AL-34662VU6067416 , YM-348 )Indenes (e.g., C-DMT )Indolizines (e.g., TACT908 (2ZEDMA) , 1ZP2MA , 1Z2MAP1O )Indolylaminopropanes (e.g., 1-API , 2-API , 4-API , 5-API (5-IT; PAL-571) , 6-API (6-IT) , 7-API )Iprindole Latrepirdine Masupirdine Medmain Molindone Non-tryptamine triptans (e.g., avitriptan , LY-334370 , naratriptan )
Phenethylamines (e.g., phenethylamine , amphetamine )Piperidinylindoles (e.g., BRL-54443 , LY-334370 , naratriptan , sertindole , SN-22 )Pirlindole Pyridinylindoles (e.g., tepirindole )Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA) , 3-pyrrolylethylamine (3-NEA) , 3-pyrrolylpropylamine )Quinolinylethylamines (e.g., mefloquine )(R )-69 (3IQ) Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g., EMD-386088 , LY-367265 , RU-24,969 )Tetrindole Tiflucarbine Tipindole Zilpaterol (RU-42173)
