Preferred IUPAC name
Methyl 4-ethyl-6,7-dimethoxy-9H-pyrido[3,4-b]indole-3-carboxylate
Other names
3D model (JSmol)
ECHA InfoCard 100.220.168 Edit this at Wikidata
  • 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
  • CCC1=C2C3=CC(=C(C=C3NC2=CN=C1C(=O)OC)OC)OC
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).
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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 GABAA 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]

See also


  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 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.
  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.