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). verify (what is ?) Infobox references

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 GABA_A 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]

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 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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v t e Convulsants
GABA receptor antagonists	Bicuculline Bicyclic phosphates (TBPS, TBPO, IPTBO) BIDN Chlorophenylsilatrane Cicutoxin Cloflubicyne Coriamyrtin Dihydropicrotoxinin DMCM EBOB Endosulfan FG-7142 Fipronil Flurothyl Gabazine Oenanthotoxin Pentylenetetrazol Phenylsilatrane Picrotoxin p-CN-TBOB p-NCS-TBOB RDX TBOB Tetramethylenedisulfotetramine Thujone Trimethylolpropane phosphite Tutin
GABA synthesis inhibitors	3-Mercaptopropionic acid 4-Deoxypyridoxine Allylglycine Crimidine Decaborane Ginkgotoxin Isoniazid Pentaborane Thiocarbohydrazide Toxopyrimidine
Glycine receptor antagonists	Coriamyrtin Dendrobine Picrotoxin Strychnine Tutin
Glutamate receptor agonists	AMPA Domoic acid Kainic acid NMDA Quisqualic acid Tetrazolylglycine
Convulsant barbiturates	CHEB Diberal (DMBB) McN-481
Other	2,2,3,3-Tetrafluoropropyl trifluoromethyl ether Bromocamphor Camphor FAZ-4 Fluoroethyl fluoroacetate MC-2973 Methionine sulfoximine Methyl fluoroacetate Nitrocyclohexane Thebaine

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^Y
3D model (JSmol)	Interactive image
ChemSpider	94746^N
ECHA InfoCard	100.220.168
IUPHAR/BPS	4179
PubChem CID	104999
UNII	1309288N1J^Y
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^N Key: GADIKQPUNWAMEB-UHFFFAOYSA-N^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). N verify (what is ^YN ?) Infobox references