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 modulators — and is used in scientific research for these properties to test new
anxiolytic and
anticonvulsant medications, respectively.
[1]
[2]
[3]
[4] It has also been shown to produce
analgesic effects in animals, which is thought to be the drug's induced
panic reducing the perception of pain.
[5]
See also
References
^ 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