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Details

Stereochemistry ACHIRAL
Molecular Formula C8H11ClN4.ClH
Molecular Weight 235.114
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MK-212 HYDROCHLORIDE

SMILES

Cl.ClC1=CN=CC(=N1)N2CCNCC2

InChI

InChIKey=PFIZGLUIYAZQFU-UHFFFAOYSA-N
InChI=1S/C8H11ClN4.ClH/c9-7-5-11-6-8(12-7)13-3-1-10-2-4-13;/h5-6,10H,1-4H2;1H

HIDE SMILES / InChI
MK-212 is a 5HT2C-receptor agonist. It displays selectivity for 5-HT2C over 5-HT2A (IC50 values are 0.028 and 0.42 uM for human 5-HT2C and 5-HT2A receptors expressed in HEK293 cells respectively). A dose-dependent the effect of 5HT2C-receptor agonist MK-212 on mouse behavior was demonstrated. Intraperitoneal injection of MK-212 in high doses (0.5 and 1.0 mg/kg) increased blood level of corticosterone in mice and reduced their motor activity. In low doses of 0.1 and 0.2 mg/kg, the agonist reduced anxiety, but had no effect on motor activity. It is hypothesized that low doses of MK-212 exhibited anxiolytic activity in mice.

Originator

Curator's Comment: # Merck

Approval Year

PubMed

PubMed

TitleDatePubMed
Serotonergic drugs, benzodiazepines and baclofen block muscimol-induced myoclonic jerks in a strain of mice.
1981 Jul 17
Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor.
1993 Mar
Serotonin(2C) receptors appear to mediate genetic sensitivity to cocaine-induced convulsions.
1999 Oct
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.
2000 Feb
Modulation of 5-HT(2A) receptor-mediated head-twitch behaviour in the rat by 5-HT(2C) receptor agonists.
2001 Jul-Aug
Activation of presynaptic 5-hydroxytryptamine 2A receptors facilitates excitatory synaptic transmission via protein kinase C in the dorsolateral septal nucleus.
2002 Sep 1
Hyperlocomotive and discriminative stimulus effects of cocaine are under the control of serotonin(2C) (5-HT(2C)) receptors in rat prefrontal cortex.
2003 Aug
Agonist actions of dihydroergotamine at 5-HT2B and 5-HT2C receptors and their possible relevance to antimigraine efficacy.
2003 Sep
Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.
2004 Aug
Anxiogenic effects in the rat elevated plus-maze of 5-HT(2C) agonists into ventral but not dorsal hippocampus.
2004 Feb
Antiallodynic effects of intrathecally administered 5-HT(2C) receptor agonists in rats with nerve injury.
2004 Mar
Contribution of serotonin (5-hydroxytryptamine; 5-HT) 5-HT2 receptor subtypes to the hyperlocomotor effects of cocaine: acute and chronic pharmacological analyses.
2004 Sep
Administration of SCH 23390 into the medial prefrontal cortex blocks the expression of MDMA-induced behavioral sensitization in rats: an effect mediated by 5-HT2C receptor stimulation and not by D1 receptor blockade.
2005 Dec
Attenuation of nicotine's discriminative stimulus effects in rats and its locomotor activity effects in mice by serotonergic 5-HT2A/2C receptor agonists.
2005 May
Behavioral effects of systemically administered MK-212 are prevented by ritanserin microinfusion into the basolateral amygdala of rats exposed to the elevated plus-maze.
2005 Nov
Updated overview of the putative role of the serotoninergic system in obsessive-compulsive disorder.
2005 Sep
Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities.
2005 Sep 28
Pharmacological characterization of 5-hydroxytryptamine-induced contraction in the chicken gastrointestinal tract.
2006 Apr
5-HT receptor subtypes involved in the anxiogenic-like action and associated Fos response of acute fluoxetine treatment in rats.
2006 Apr
Serotonin2C receptors (5-HT2C R) control expression of cocaine-induced conditioned hyperactivity.
2006 Feb 28
Possible involvement of spinal noradrenergic mechanisms in the antiallodynic effect of intrathecally administered 5-HT2C receptor agonists in the rats with peripheral nerve injury.
2007 Jul 12
Impact of RNA editing on functions of the serotonin 2C receptor in vivo.
2010
5-HT2C receptor agonists attenuate pain-related behaviour in a rat model of trigeminal neuropathic pain.
2010 Nov
Spontaneous rhythmogenic capabilities of sympathetic neuronal assemblies in the rat spinal cord slice.
2010 Oct 27
Locomotor response to L-DOPA in reserpine-treated rats following central inhibition of aromatic L-amino acid decarboxylase: further evidence for non-dopaminergic actions of L-DOPA and its metabolites.
2010 Sep
Stimulation of medial prefrontal cortex serotonin 2C (5-HT(2C)) receptors attenuates cocaine-seeking behavior.
2010 Sep
Patents

Sample Use Guides

The effects of MK-212 (10, 20, and 40 mg, orally), a centrally acting serotonin (5-HT) receptor agonist and placebo, on serum cortisol, prolactin, and growth hormone levels were studied in eight healthy men over 3-hr. MK-212 produced a dose-related increase in serum cortisol levels, with the 20- and 40-mg doses producing significant elevations. Serum prolactin levels were significantly elevated only by the 40-mg dose.
Route of Administration: Oral
In Vitro Use Guide
MK-212 (1 x 10(-7)M -- 1 x 10(-5)M) produced dose-dependent contractions of guinea pig ileum, taenia coil and rat fundus strip.
Name Type Language
MK-212 HYDROCHLORIDE
Common Name English
PYRAZINE, 2-CHLORO-6-(1-PIPERAZINYL)-, HYDROCHLORIDE
Systematic Name English
PYRAZINE, 2-CHLORO-6-(1-PIPERAZINYL)-, HYDROCHLORIDE (1:1)
Systematic Name English
MK-212 HCL
Code English
MK-212-HCL
Code English
PYRAZINE, 2-CHLORO-6-(1-PIPERAZINYL)-, MONOHYDROCHLORIDE
Systematic Name English
Code System Code Type Description
DRUG BANK
DBSALT002137
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
CAS
67250-10-6
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
NON-SPECIFIC STOICHIOMETRY
EPA CompTox
DTXSID60210668
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
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FDA UNII
8722D514RX
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
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ECHA (EC/EINECS)
262-883-0
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
PUBCHEM
198421
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
PRIMARY
CAS
61655-58-1
Created by admin on Fri Dec 15 15:01:59 GMT 2023 , Edited by admin on Fri Dec 15 15:01:59 GMT 2023
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