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MedKoo Cat#: 523128 | Name: Perlapine
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Perlapine is a potent and selective hM3Dq DREADD agonist (EC50 = 2.8 nM). Perlapine exhibits >10,000-fold selectivity for hM3Dq over hM3. Perlapine is an atypical neuroleptic and a structural analogue of clozapine.

Chemical Structure

Perlapine
CAS#1977-11-3

Theoretical Analysis

MedKoo Cat#: 523128

Name: Perlapine

CAS#: 1977-11-3

Chemical Formula: C19H21N3

Exact Mass: 291.1736

Molecular Weight: 291.40

Elemental Analysis: C, 78.32; H, 7.26; N, 14.42

Price and Availability

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1mg USD 250.00 2 Weeks
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Related CAS #
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Synonym
Perlapine; Hypnodin; Perlapina; NSC291840; NSC 291840; NSC-291840; AW142333; AW 142333; AW-142333;
IUPAC/Chemical Name
6-(4-Methyl-1-piperazinyl)-11H-dibenz[b,e]azepine
InChi Key
PWRPUAKXMQAFCJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H21N3/c1-21-10-12-22(13-11-21)19-17-8-4-2-6-15(17)14-16-7-3-5-9-18(16)20-19/h2-9H,10-14H2,1H3
SMILES Code
CN1CCN(C2=NC3=CC=CC=C3CC4=CC=CC=C42)CC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Perlapine is a potent and selective hM3Dq DREADD agonist (EC50 = 2.8 nM).
In vitro activity:
From this screen, this study discovered perlapine as a novel, potent agonist of hM3Dq (Figure (Figure3).3). Importantly, perlapine was >10 000-fold selective for hM3Dq over hM3. Interestingly, perlapine contains a different tricyclic core in comparison with CNO. The high hM3Dq potency of perlapine suggests that the benzodiazepine tricyclic core of the CNO (compound 5a) scaffold is not required for maintaining high hM3Dq agonist activity. Reference: ACS Chem Neurosci. 2015 Mar 18;6(3):476-84. https://pubmed.ncbi.nlm.nih.gov/25587888/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMF 10.0 34.32
DMSO 12.3 42.16
DMSO:PBS (pH 7.2) (1:1) 0.5 1.72
Ethanol 5.0 17.16
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 291.40 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Chen X, Choo H, Huang XP, Yang X, Stone O, Roth BL, Jin J. The first structure-activity relationship studies for designer receptors exclusively activated by designer drugs. ACS Chem Neurosci. 2015 Mar 18;6(3):476-84. doi: 10.1021/cn500325v. Epub 2015 Jan 27. PMID: 25587888; PMCID: PMC4368042.
In vitro protocol:
Chen X, Choo H, Huang XP, Yang X, Stone O, Roth BL, Jin J. The first structure-activity relationship studies for designer receptors exclusively activated by designer drugs. ACS Chem Neurosci. 2015 Mar 18;6(3):476-84. doi: 10.1021/cn500325v. Epub 2015 Jan 27. PMID: 25587888; PMCID: PMC4368042.
In vivo protocol:
TBD
1: Kljakic O, Hogan-Cann AE, Yang H, Dover B, Al-Onaizi M, Prado MAM, Prado VF. Chemogenetic activation of VGLUT3-expressing neurons decreases movement. Eur J Pharmacol. 2022 Nov 15;935:175298. doi: 10.1016/j.ejphar.2022.175298. Epub 2022 Oct 2. PMID: 36198338. 2: Weston M, Kaserer T, Wu A, Mouravlev A, Carpenter JC, Snowball A, Knauss S, von Schimmelmann M, During MJ, Lignani G, Schorge S, Young D, Kullmann DM, Lieb A. Olanzapine: A potent agonist at the hM4D(Gi) DREADD amenable to clinical translation of chemogenetics. Sci Adv. 2019 Apr 17;5(4):eaaw1567. doi: 10.1126/sciadv.aaw1567. PMID: 31001591; PMCID: PMC6469940. 3: Chen X, Choo H, Huang XP, Yang X, Stone O, Roth BL, Jin J. The first structure-activity relationship studies for designer receptors exclusively activated by designer drugs. ACS Chem Neurosci. 2015 Mar 18;6(3):476-84. doi: 10.1021/cn500325v. Epub 2015 Jan 27. PMID: 25587888; PMCID: PMC4368042. 4: Seeman P, Tallerico T. Antipsychotic drugs which elicit little or no parkinsonism bind more loosely than dopamine to brain D2 receptors, yet occupy high levels of these receptors. Mol Psychiatry. 1998 Mar;3(2):123-34. doi: 10.1038/sj.mp.4000336. PMID: 9577836. 5: Carey GJ, Bergman J. Discriminative-stimulus effects of clozapine in squirrel monkeys: comparison with conventional and novel antipsychotic drugs. Psychopharmacology (Berl). 1997 Aug;132(3):261-9. doi: 10.1007/s002130050344. PMID: 9292626. 6: Seeman P, Corbett R, Van Tol HH. Atypical neuroleptics have low affinity for dopamine D2 receptors or are selective for D4 receptors. Neuropsychopharmacology. 1997 Feb;16(2):93-110; discussion 111-35. doi: 10.1016/S0893-133X(96)00187-X. PMID: 9015795. 7: Seeman P, Corbett R, Nam D, Van Tol HH. Dopamine and serotonin receptors: amino acid sequences, and clinical role in neuroleptic parkinsonism. Jpn J Pharmacol. 1996 Jul;71(3):187-204. doi: 10.1254/jjp.71.187. PMID: 8854201. 8: Altar CA, Boyar WC, Wasley A, Gerhardt SC, Liebman JM, Wood PL. Dopamine neurochemical profile of atypical antipsychotics resembles that of D-1 antagonists. Naunyn Schmiedebergs Arch Pharmacol. 1988 Aug;338(2):162-8. doi: 10.1007/BF00174864. PMID: 2903451. 9: Dougan DF, Wade DN. Octopamine receptors in the molluscan aortic bulb: effects of clozapine and chlordimeform. Comp Biochem Physiol C Comp Pharmacol Toxicol. 1985;82(1):193-7. doi: 10.1016/0742-8413(85)90228-2. PMID: 2865061. 10: Spealman RD. Effects of some dibenzo-azepines on suppressed and nonsuppressed behavior of squirrel monkeys. Psychopharmacology (Berl). 1985;85(2):129-32. doi: 10.1007/BF00428400. PMID: 2861615. 11: Liebman JM, Neale R, Noreika L, Braunwalder A. Differential reversal of various dopamine antagonists by anticholinergics in Sidman avoidance: possible relationship to adrenergic blockade. Psychopharmacology (Berl). 1981;75(3):248-53. doi: 10.1007/BF00432433. PMID: 6119730. 12: Lin CW, Maayani S, Wilk S. The effect of typical and atypical neuroleptics on binding of [3H]spiroperidol in calf caudate. J Pharmacol Exp Ther. 1980 Mar;212(3):462-8. PMID: 6102144. 13: Meltzer HY, Fessler RG, Fang VS. Perlapine: relationship between stimulation of prolactin secretion and antipsychotic activity. Psychopharmacology (Berl). 1977 Oct 20;54(2):183-6. doi: 10.1007/BF00426777. PMID: 412213. 14: Wilk S, Stanley M. Perlapine and dopamine metabolism: prediction of antipsychotic efficacy. Eur J Pharmacol. 1977 Jan 7;41(1):65-72. doi: 10.1016/0014-2999(77)90372-7. PMID: 12986. 15: Bürki HR, Sayers AC, Ruch W, Asper H. Effects of clozapine and other dibenzo-epines on central dopaminergic and cholinergic systems. Structure- activity relationships. Arzneimittelforschung. 1977;27(8):1561-5. PMID: 20900. 16: Miller RJ, Hiley CR. Anti-dopaminergic and anti-muscarinic effects of dibenzodiazepines: relationship to drug induced Parkinsonism. Naunyn Schmiedebergs Arch Pharmacol. 1976;292(3):289-93. doi: 10.1007/BF00517391. PMID: 7753. 17: Bürki HR, Ruch W, Asper H. Effects of clozapine, thioridazine, perlapine and haloperidol on the metabolism of the biogenic amines in the brain of the rat. Psychopharmacologia. 1975;41(1):27-33. doi: 10.1007/BF00421302. PMID: 235767. 18: Allen SR, Oswald I. The effects of perlapine on sleep. Psychopharmacologia. 1973 Aug 22;32(1):1-9. doi: 10.1007/BF00421703. PMID: 4359662. 19: Stille G, Sayers A, Lauener H, Eichenberger E. 6-(4-Methyl-1-piperazinyl)morphanthridine (Perlapine), a new tricyclic compound with sedative and sleep-promoting properties. A pharmacological study. Psychopharmacologia. 1973 Feb 20;28(4):325-37. doi: 10.1007/BF00422753. PMID: 4695567.