From Wikipedia, the free encyclopedia
DMCM
Names
Preferred IUPAC name
Methyl 4-ethyl-6,7-dimethoxy-9H -pyrido[3,4-b ]indole-3-carboxylate
Other names
DMCM
Identifiers
ChemSpider
ECHA InfoCard 100.220.168
UNII
InChI=1S/C17H18N2O4/c1-5-9-15-10-6-13(21-2)14(22-3)7-11(10)19-12(15)8-18-16(9)17(20)23-4/h6-8,19H,5H2,1-4H3
N Key: GADIKQPUNWAMEB-UHFFFAOYSA-N
N
CCC1=C2C3=CC(=C(C=C3NC2=CN=C1C(=O)OC)OC)OC
Properties
C17 H18 N2 O4
Molar mass
314.336 g/mol
Boiling point
87 °C (189 °F; 360 K)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
DMCM (methyl 6,7-dimethoxy-4-ethyl-β-carboline-3-carboxylate ) is a drug from the β-carboline family that induces anxiety and convulsions by acting as a negative allosteric modulator of GABAA receptors — functionally opposite to benzodiazepines and related drugs which are positive allosteric modulatorsanxiolytic and anticonvulsant medications, respectively.[ 1] [ 2] [ 3] [ 4] analgesic effects in animals, which is thought to be the drug's induced panic reducing the perception of pain.[ 5]
^ Cole, BJ; Hillmann, M; Seidelmann, D; Klewer, M; Jones, GH (1995). "Effects of benzodiazepine receptor partial inverse agonists in the elevated plus maze test of anxiety in the rat". Psychopharmacology . 121 (1): 118– 26. doi :10.1007/BF02245598 . PMID 8539336 . S2CID 25423119 . ^ Brodie, MJ (1995). "Tiagabine pharmacology in profile". Epilepsia . 36 (Suppl 6): S7 – S9 . doi :10.1111/j.1528-1157.1995.tb06015.x . PMID 8595791 . S2CID 27336198 . ^ De Sarro, G; Chimirri, A; McKernan, R; Quirk, K; Giusti, P; De Sarro, A (1997). "Anticonvulsant activity of azirino[1,2-d ][1,4]benzodiazepines and related 1,4-benzodiazepines in mice". Pharmacology Biochemistry and Behavior . 58 (1): 281– 9. doi :10.1016/S0091-3057(96)00565-5 . PMID 9264104 . S2CID 24492818 . ^ Leppä, E; Vekovischeva, OY; Lindén, AM; Wulff, P; Oberto, A; Wisden, W; Korpi, ER (2005). "Agonistic effects of the β-carboline DMCM revealed in GABAA receptor γ2 subunit F77I point-mutated mice". Neuropharmacology . 48 (4): 469– 78. doi :10.1016/j.neuropharm.2004.11.007 . PMID 15755475 . S2CID 54340687 . ^ Sieve, AN; King, TE; Ferguson, AR; Grau, JW; Meagher, MW (2001). "Pain and negative affect: evidence the inverse benzodiazepine agonist DMCM inhibits pain and learning in rats". Psychopharmacology . 153 (2): 180– 90. doi :10.1007/s002130000535 . PMID 11205417 . S2CID 2591731 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see here for a full list): α-EMTBL Alcohols (e.g., drinking alcohol , 2M2B )Anabolic steroids Avermectins (e.g., ivermectin )Barbiturates (e.g., phenobarbital )Benzodiazepines (e.g., diazepam )Bromide compounds (e.g., potassium bromide )Carbamates (e.g., meprobamate )Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine) )Etazepine Etifoxine Fenamates (e.g., mefenamic acid )Flavonoids (e.g., apigenin , hispidulin )Fluoxetine Flupirtine Imidazoles (e.g., etomidate )Kava constituents (e.g., kavain )Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone , cholesterol , THDOC )Niacin Niacinamide Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil ), cyclopyrrolones (e.g., zopiclone ), imidazopyridines (e.g., zolpidem ), pyrazolopyrimidines (e.g., zaleplon ))Norfluoxetine Petrichloral Phenols (e.g., propofol )Phenytoin Piperidinediones (e.g., glutethimide )Propanidid Pyrazolopyridines (e.g., etazolate )Quinazolinones (e.g., methaqualone )Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin )Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal) )Topiramate Valerian constituents (e.g., valerenic acid )Volatiles /gases (e.g., chloral hydrate , chloroform , diethyl ether , paraldehyde , sevoflurane )Negative modulators: 1,3M1B 3M2B 11-Ketoprogesterone 17-Phenylandrostenol α3IA α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Anabolic steroids Amiloride Anisatin β-Lactams (e.g., penicillins , cephalosporins , carbapenems )Basmisanil Bemegride Bicyclic phosphates (TBPS , TBPO , IPTBO )BIDN Bilobalide Bupropion CHEB Chlorophenylsilatrane Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil )Flavonoids (e.g., amentoflavone , oroxylin A )Flumazenil Fluoroquinolones (e.g., ciprofloxacin )Flurothyl Furosemide Golexanolone Iomazenil (123 I) IPTBO Isopregnanolone (sepranolone) L-655,708 Laudanosine Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Nonsteroidal antiandrogens (e.g., apalutamide , bicalutamide , enzalutamide , flutamide , nilutamide )Oenanthotoxin Pentylenetetrazol (pentetrazol) Phenylsilatrane Picrotoxin (i.e., picrotin , picrotoxinin and dihydropicrotoxinin )Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426 GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor
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) , 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)
