CAS 52-52-8|Cycloleucine
Introduction：Basic information about CAS 52-52-8|Cycloleucine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Cycloleucine | ||
|---|---|---|---|
| CAS Number | 52-52-8 | Molecular Weight | 129.157 |
| Density | 1.2±0.1 g/cm3 | Boiling Point | 256.1±23.0 °C at 760 mmHg |
| Molecular Formula | C6H11NO2 | Melting Point | 320 °C (dec.)(lit.) |
| MSDS | ChineseUSA | Flash Point | 108.7±22.6 °C |
| Symbol | GHS06 | Signal Word | Danger |
Names
| Name | 1-aminocyclopentanecarboxylic acid |
|---|---|
| Synonym | More Synonyms |
Cycloleucine BiologicalActivity
| Description | Cycloleucine is a specific inhibitor of S-adenosyl-methionine mediated methylation. Cycloleucine is antagonist of NMDA receptor associated glycine receptor, with a Ki of 600 μM. Cycloleucine is also a competitive inhibitor of ATP: L-methionine-S-adenosyl transferase in vitro. Cycloleucine has anxiolytic and cytostatic effects[1][2][3][4]. |
|---|---|
| Related Catalog | Signaling Pathways >>Neuronal Signaling >>iGluRResearch Areas >>CancerResearch Areas >>InfectionResearch Areas >>Metabolic DiseaseResearch Areas >>Neurological DiseaseSignaling Pathways >>Membrane Transporter/Ion Channel >>iGluR |
| Target | Ki: 600 μM (NMDA)[1][2] |
| In Vitro | Cycloleucine (4-40 mM; 3 h) blocks internal methylation of viral RNA in B77 transformed chick embryo fibroblasts[5]. Cycloleucine (40 mM; 24 h) blocks the formation of both m6A and the penultimate Gm in B77 38S RNA subunits by greater than 90%[5]. Cytostatic (10 µg/mL) inhibits the viability human KB and mouse L1210s leukemia cell lines[5]. |
| In Vivo | Cycloleucine (0.5-4 µg; intracerebroventrical injection) increases time spent in open arms, open arm entries, and extreme arrivals in rats[3]. Animal Model: Male rats bilaterally cannulated into the nucleus accumbens septi (NAS)[3] Dosage: 1 µL of 0.5, 1.0, 2.0, 4 µg/µL Administration: Intracerebroventrical injection Result: Increased time spent in the open arms and extreme arrivals at all doses. Increased open arm entries at the dose of 4 μg. |
| References | [1]. Hood WF, et, al. 1-Aminocyclobutane-1-carboxylate (ACBC): a specific antagonist of the N-methyl-D-aspartate receptor coupled glycine receptor. Eur J Pharmacol. 1989 Feb 28;161(2-3):281-2. [2]. Caboche M, et, al. RNA methylation and control of eukaryotic RNA biosynthesis. Effects of cycloleucine, a specific inhibitor of methylation, on ribosomal RNA maturation. Eur J Biochem. 1977 Mar 15;74(1):19-29. [3]. Gargiulo API, et, al. Effects of Cycloleucine in the Nucleus Accumbens Septi on the Elevated plus Maze Test in Rats. Neuropsychobiology. 2020;79(3):191-197. [4]. Duś D, et, al. Cytostatic activity in vitro of cycloleucine, aspartic acid and glutamic acid phosphonic analogues. Arch Immunol Ther Exp (Warsz). 1980;28(3):433-8. [5]. Dimock K, et, al. Cycloleucine blocks 5'-terminal and internal methylations of avian sarcoma virus genome RNA. Biochemistry. 1978 Aug 22;17(17):3627-32. |
Chemical & Physical Properties
| Density | 1.2±0.1 g/cm3 |
|---|---|
| Boiling Point | 256.1±23.0 °C at 760 mmHg |
| Melting Point | 320 °C (dec.)(lit.) |
| Molecular Formula | C6H11NO2 |
| Molecular Weight | 129.157 |
| Flash Point | 108.7±22.6 °C |
| Exact Mass | 129.078979 |
| PSA | 63.32000 |
| LogP | -0.05 |
| Vapour Pressure | 0.0±1.1 mmHg at 25°C |
| Index of Refraction | 1.522 |
| InChIKey | NILQLFBWTXNUOE-UHFFFAOYSA-N |
| SMILES | NC1(C(=O)O)CCCC1 |
| Water Solubility | 5 g/100 mL |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Human
- DOSE/DURATION :
- 60 mg/kg
- TOXIC EFFECTS :
- Behavioral - anorexia (human) Gastrointestinal - nausea or vomiting
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 290 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 340 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 309 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 119 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 375 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. (Bethesda, MD 20205) Volume(issue)/page/year: JAN1986
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 300 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- LDLo - Lowest published lethal dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - cat
- DOSE/DURATION :
- 4 gm/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,469,1971
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - guinea pig
- DOSE/DURATION :
- 140 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Bird - quail
- DOSE/DURATION :
- >316 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- EESADV Ecotoxicology and Environmental Safety. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1977- Volume(issue)/page/year: 6,149,1982 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 4200 mg/kg/4W-C
- TOXIC EFFECTS :
- Blood - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 948 mg/kg/30D-I
- TOXIC EFFECTS :
- Behavioral - food intake (animal) Musculoskeletal - other changes
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 900 mg/kg/15D-I
- TOXIC EFFECTS :
- Behavioral - muscle weakness Gastrointestinal - other changes Blood - hemorrhage
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Primate - monkey
- DOSE/DURATION :
- 7200 mg/kg/30D-I
- TOXIC EFFECTS :
- Behavioral - muscle weakness Related to Chronic Data - death
- REFERENCE :
- JMPCAS Journal of Medicinal and Pharmaceutical Chemistry. (Washington, DC) V.1-5, 1959-62. For publisher information, see JMCMAR. Volume(issue)/page/year: 3,1,1961
Safety Information
| Symbol | GHS06 |
|---|---|
| Signal Word | Danger |
| Hazard Statements | H301 |
| Precautionary Statements | P301 + P310 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Faceshields;Gloves |
| Hazard Codes | Xn:Harmful |
| Risk Phrases | R22 |
| Safety Phrases | S22-S24/25 |
| RIDADR | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | GY2625000 |
| Packaging Group | III |
| Hazard Class | 6.1 |
| HS Code | 2922499990 |
Customs
| HS Code | 2922499990 |
|---|---|
| Summary | HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0% |
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Synonyms
| 1-Aminocyclopentanecarboxylicacid |
| 1-aminocyclopentane-1-carboxylic acid |
| 1-Aminocyclopropane-1-carboxylic acid |
| EINECS 200-144-6 |
| 1-amino-1-carboxylic cyclopentane |
| 1-Amino-1-cyclopentanecarboxylic acid |
| ACPC |
| Cyclopentanecarboxylic acid, 1-amino- |
| MFCD00001381 |
| Cycloleucine |
| 1-amino-1-carboxycyclopentane |
| Cyclolencine |
| 1-Aminocyclopentanecarboxylic acid |
| 1-Amino-1-cyclopentanecarboxylate |
| 1-aminocyclopentane-1-carboxylicacid |
