DMCM

DMCM
Names
	Preferred IUPAC name Methyl 4-ethyl-6,7-dimethoxy-9H-pyrido[3,4-b]indole-3-carboxylate
	Other names DMCM
Identifiers
CAS Number	82499-00-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	94746 ;
ECHA InfoCard	100.220.168
IUPHAR/BPS	4179;
PubChem CID	104999;
UNII	1309288N1J ;
CompTox Dashboard (EPA)	DTXSID90896999 ;
	InChI 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 Key: GADIKQPUNWAMEB-UHFFFAOYSA-N ;
	SMILES CCC1=C2C3=CC(=C(C=C3NC2=CN=C1C(=O)OC)OC)OC;
Properties
Chemical formula	C17H18N2O4
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).
	(what is ?)
	Infobox references

DMCM (methyl 6,7-dimethoxy-4-ethyl-β-carboline-3-carboxylate) is a drug from the β-carboline family. It acts as a negative allosteric modulator of GABA_A receptors, meaning that it causes the opposite effects to the benzodiazepine class of drugs. As such, DMCM has anxiogenic and convulsant properties,^[1] and is used in scientific research to induce anxiety so that new anxiolytic medications can be tested,^[2] and to produce convulsions so that anticonvulsant medications can be tested.^[3]^[4]^[5] It has also been shown to produce analgesic effects in animals, thought to be because it produces panic which reduces the perception of pain.^[6]

References[]

^ Contó, MB; De Carvalho, JG; Benedito, MA (2005). "Behavioral differences between subgroups of rats with high and low threshold to clonic convulsions induced by DMCM, a benzodiazepine inverse agonist". Pharmacology Biochemistry and Behavior. 82 (3): 417–26. doi:10.1016/j.pbb.2005.09.012. PMID 16297441. S2CID 8157142.
^ 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 GABA_A 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.

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[1] Contó, MB; De Carvalho, JG; Benedito, MA (2005). "Behavioral differences between subgroups of rats with high and low threshold to clonic convulsions induced by DMCM, a benzodiazepine inverse agonist". Pharmacology Biochemistry and Behavior. 82 (3): 417–26. doi:10.1016/j.pbb.2005.09.012. PMID 16297441. S2CID 8157142.

[2] 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.

[3] 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.

[4] 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.

[5] Leppä, E; Vekovischeva, OY; Lindén, AM; Wulff, P; Oberto, A; Wisden, W; Korpi, ER (2005). "Agonistic effects of the β-carboline DMCM revealed in GABA_A receptor γ2 subunit F77I point-mutated mice". Neuropharmacology. 48 (4): 469–78. doi:10.1016/j.neuropharm.2004.11.007. PMID 15755475. S2CID 54340687.

[6] 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.

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v t Convulsants
GABA receptor antagonists	Picrotoxin Gabazine Tetramethylenedisulfotetramine Cicutoxin Phenylsilatrane Tutin Pentylenetetrazol Thujone Endosulfan Bicuculline Oenanthotoxin Fipronil EBOB BIDN Dihydropicrotoxinin DMCM FG-7142 Chlorophenylsilatrane Bicyclic phosphates (TBPS, TBPO, IPTBO) Flurothyl Trimethylolpropane phosphite Cloflubicyne
GABA synthesis inhibitors	Allylglycine Crimidine Ginkgotoxin Toxopyrimidine Isoniazid 3-Mercaptopropionic acid 4-Deoxypyridoxine Pentaborane Decaborane Thiocarbohydrazide
Glycine receptor antagonists	Strychnine Tutin Picrotoxin Dendrobine
Glutamate receptor agonists	AMPA NMDA Kainic acid Domoic acid Quisqualic acid Tetrazolylglycine
Other	Methyl fluoroacetate Fluoroethyl fluoroacetate Nitrocyclohexane Methionine sulfoximine Thebaine Camphor

DMCM

See also[]

References[]