(+)-cis-2-Aminomethylcyclopropane carboxylic acid

Not to be confused with Cyclic adenosine monophosphate.

(+)-*cis*-2-Aminomethylcyclopropane carboxylic acid
Names


Systematic IUPAC name (1S,2R)-2-(Aminomethyl)cyclopropane-1-carboxylic acid^[1]
Identifiers
CAS Number	36489-13-1^N
ChEMBL	ChEMBL230115^Y
ChemSpider	1236854^Y
Jmol interactive 3D	Image
PubChem	1502041
InChI InChI=1S/C5H9NO2/c6-2-3-1-4(3)5(7)8/h3-4H,1-2,6H2,(H,7,8)/t3-,4-/m0/s1^Y Key: QUFMERRXRMSAPZ-IMJSIDKUSA-N^Y
SMILES NC[C@@H]1C[C@@H]1C(O)=O
Properties
Chemical formula	C₅H₉NO₂
Molar mass	115.13 g·mol⁻¹
Density	1.275 g/mL
Boiling point	256.9 °C (494.4 °F; 530.0 K)
log P	−0.721
Acidity (pK_a)	4.157
Basicity (pK_b)	9.840
Isoelectric point	7.01
Related compounds
Related cycloalkanes	ACPD
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

(+)-cis-2-Aminomethylcyclopropane carboxylic acid ((+)-CAMP) is a agonist for the GABAA-rho receptor.^[2]^[3]

References

↑ "AC1LT400 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 11 July 2005. Identification and Related Records. Retrieved 7 October 2011.
↑ Duke, RK; Chebib, M; Balcar, VJ; Allan, RD; Mewett, KN; Johnston, GA (2000). "(+)- and (−)-cis-2-aminomethylcyclopropanecarboxylic acids show opposite pharmacology at recombinant rho(1) and rho(2) GABA(C) receptors". Journal of Neurochemistry 75 (6): 2602–10. doi:10.1046/j.1471-4159.2000.0752602.x. PMID 11080214.
↑ Carland, JE; Moorhouse, AJ; Barry, PH; Johnston, GA; Chebib, M (2004). "Charged residues at the 2' position of human GABAC rho 1 receptors invert ion selectivity and influence open state probability". The Journal of Biological Chemistry 279 (52): 54153–60. doi:10.1074/jbc.M410625200. PMID 15485818.

GABAergics

Receptor
(ligands)

GABA_A

Agonists	(+)-Catechin Bamaluzole Barbiturates (e.g., phenobarbital) BL-1020 DAVA Dihydromuscimol GABA Gabamide GABOB Gaboxadol (THIP) Homotaurine (tramiprosate, 3-APS) Ibotenic acid iso-THAZ iso-THIP Isoguvacine Isomuscimol Isonipecotic acid Kojic amine Lignans (e.g., honokiol) Monastrol Muscimol Neuroactive steroids (e.g., allopregnanolone) Org 20599 Phenibut Picamilon P4S Progabide Propofol Quisqualamine SL-75102 TACA TAMP Terpenoids (e.g., borneol) Thiomuscimol Tolgabide ZAPA

PAMs	(abridged; see here for a full list): α-EMTBL Alcohols (e.g., ethanol) Avermectins (e.g., ivermectin) Barbiturates (e.g., phenobarbital) Benzodiazepines (e.g., diazepam) Bromide compounds (e.g., potassium bromide) Carbamates (e.g., meprobamate) Carbamazepine Chloralose Chlormezanone Clomethiazole Dihydroergolines (e.g., ergoloid (dihydroergotoxine)) Etazepine Etifoxine Fenamates (e.g., mefenamic acid) Flavonoids (e.g., apigenin, hispidulin) Fluoxetine Flupirtine Imidazoles (e.g., etomidate) Kava constituents (e.g., kavain) Lanthanum Loreclezole Monastrol Neuroactive steroids (e.g., allopregnanolone, cholesterol) Niacin Nicotinamide (niacinamide) Nonbenzodiazepines (e.g., β-carbolines (e.g., abecarnil), cyclopyrrolones (e.g., zopiclone), imidazopyridines (e.g., zolpidem), pyrazolopyrimidines (e.g., zaleplon)) Norfluoxetine Petrichloral Phenols (e.g., propofol) Phenytoin Piperidinediones (e.g., glutethimide) Propanidid Pyrazolopyridines (e.g., etazolate) Quinazolinones (e.g., methaqualone) Retigabine (ezogabine) ROD-188 Skullcap constituents (e.g., baicalin) Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal)) Topiramate Valerian constituents (e.g., valerenic acid) Volatiles/gases (e.g., chloral hydrate, chloroform, diethyl ether, paraldehyde, sevoflurane)

Antagonists	Bicuculline Coriamyrtin Dihydrosecurinine Gabazine (SR-95531) Hydrastine Hyenachin (mellitoxin) PHP-501 Pitrazepin Securinine Sinomenine SR-42641 SR-95103 Thiocolchicoside Tutin

NAMs	1,3M1B 3M2B 17-Phenylandrostenol α5IA (LS-193,268) β-CCB β-CCE β-CCM β-CCP β-EMGBL Amiloride Anisatin β-Lactams (e.g., penicillins, cephalosporins, carbapenems) Basmisanil Bemegride Bilobalide CHEB Cicutoxin Cloflubicyne Cyclothiazide DHEA DHEA-S Dieldrin (+)-DMBB DMCM DMPC EBOB Etbicyphat FG-7142 (ZK-31906) Fiproles (e.g., fipronil) Flavonoids (e.g., amentoflavone, oroxylin A) Flumazenil Fluoroquinolones (e.g., ciprofloxacin) Flurothyl Furosemide Iomazenil (¹²³I) Isoallopregnanolone Isopregnanolone (sepranolone) L-655,708 Laudanosine Leptazol Lindane MaxiPost Morphine Morphine-3-glucuronide MRK-016 Naloxone Naltrexone Nicardipine Non-steroidal antiandrogens (e.g., apalutamide, bicalutamide, enzalutamide, flutamide, nilutamide) Oenanthotoxin Pentetrazol (metrazol) Phenylsilatrane Picrotoxin (i.e., picrotin and picrotoxinin) Pregnenolone sulfate Propybicyphat PWZ-029 Radequinil Ro 15-4513 Ro 19-4603 RO4882224 RO4938581 Sarmazenil SCS Suritozole TB-21007 TBOB TBPS TCS-1105 Terbequinil TETS Thujone U-93631 Zinc ZK-93426

GABA_A-ρ

Agonists	BL-1020 CACA CAMP Homohypotaurine GABA GABOB Ibotenic acid Isoguvacine Muscimol N⁴-Chloroacetylcytosine arabinoside Picamilon Progabide TACA TAMP Thiomuscimol Tolgabide

PAMs	Allopregnanolone Alphaxolone ATHDOC Lanthanides

Antagonists	(S)-2-MeGABA (S)-4-ACPBPA (S)-4-ACPCA 2-MeTACA 3-APMPA 4-ACPAM 4-GBA cis-3-ACPBPA CGP-36742 (SGS-742) DAVA Gabazine (SR-95531) Gaboxadol (THIP) I4AA Isonipecotic acid Loreclezole P4MPA P4S SKF-97541 SR-95318 SR-95813 TPMPA trans-3-ACPBPA ZAPA

NAMs	5α-Dihydroprogesterone Bilobalide Loreclezole Picrotoxin (picrotin, picrotoxinin) Pregnanolone ROD-188 THDOC Zinc

GABA_B

Agonists	1,4-Butanediol Aceburic acid Arbaclofen Arbaclofen placarbil Baclofen BL-1020 GABA Gabamide GABOB GBL GHB GHBAL GHV GVL Isovaline Lesogaberan Phenibut Picamilon Progabide Sodium oxybate SKF-97,541 SL 75102 Tolgabide

Antagonists	2-Hydroxysaclofen CGP-35348 CGP-46381 CGP-52432 CGP-54626 CGP-55845 CGP-64213 DAVA Homotaurine (tramiprosate, 3-APS) Phaclofen Saclofen SCH-50911 SKF-97541

NAMs	Compound 14

PAMs	ADX-71441 BHF-177 BHFF BSPP CGP-7930 CGP-13501 GS-39783 rac-BHFF

Transporter
(blockers)

GAT	4-Aminovaleric acid β-Alanine Arecaidine CI-966 DABA Deramciclane (EGIS-3886, EGYT-3886) EF-1502 Gabaculine Guvacine Ibotenic acid Muscimol Nipecotic acid NNC 05-2090 NO-711 Riluzole SKF-89976A SNAP-5114 TACA Tiagabine

VIAAT	β-Alanine Bafilomycin A1 Chicago sky blue 6B Evans blue GABA Glycine N-Butyric acid Nigericin Nipecotic acid Valinomycin Vigabatrin

Enzyme
(inhibitors)

GAD	3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide

GABA-T	3-Hydrazinopropionic acid γ-Acetylenic-GABA AOAA EOS Gabaculine Isoniazid L-Cycloserine Phenelzine PEH Rosmarinic acid (lemon balm) Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (divalproex sodium) Valproic acid Valpromide Vigabatrin

Others

Precursors	1,4-Butanediol GHB GHBAL Glutamate Glutamine

Analogues	Pregabalin 4-Methylpregabalin Atagabalin Gabapentin Gabapentin enacarbil Imagabalin Mirogabalin PD-200,347 PD-217,014 PD-299,685 Phenibut

Others	Vitamin B₆ GABA-T activators: 3-Methyl-GABA

See also: GHBergics • Glutamatergics • Glycinergics

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