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68-41-7

Basic Information
CAS No.: 68-41-7
Name: D-Cycloserine
Article Data: 37
Molecular Structure:
Molecular Structure of 68-41-7 (D-Cycloserine)
Formula: C3H6N2O2
Molecular Weight: 102.093
Synonyms: 3-Isoxazolidinone,4-amino-, (+)- (8CI);3-Isoxazolidinone, 4-amino-, (R)-;(+)-Cycloserine;(4R)-4-Amino-3-isoxazolidinone;(R)-4-Amino-3-isoxazolidinone;(R)-Cycloserine;Cyclo-D-serine;Cycloserine;D-4-Amino-3-isoxazolidinone;D-4-Amino-3-isoxazolidone;D-CS;Farmiserina;Micoserina;Miroseryn;NSC 154851;Novoserin;Orientomycin;Oxamycin;Seromycin;Tisomycin;Wasserina;D-Cycloserine;
EINECS: 200-688-4
Density: 1.278 g/cm3
Melting Point: 147ºC
Boiling Point: 267ºC
Solubility: soluble in water
Appearance: White to pale yellow cryst. powder
Hazard Symbols: HarmfulXn
Risk Codes: 5-20
Safety: 38-36/37-24/25
PSA: 64.35000
LogP: -0.59580
Synthetic route
17136-54-8

Methyl (2R)-2-amino-3-chloropropionate hydrochloride

68-41-7

cycloserine

Conditions
ConditionsYield
With hydrogenchloride; acetone oxime In methanol at 65℃; for 1h; Temperature;94.25%
29491-80-3

methyl (2R)-2-amino-3-(aminooxy)propanoate

68-41-7

cycloserine

Conditions
ConditionsYield
Stage #1: methyl (2R)-2-amino-3-(aminooxy)propanoate With sodium hydroxide In water at -5 - 0℃; for 3h;
Stage #2: With acetic acid In water; isopropyl alcohol at -12 - -8℃; for 1h; pH=6.7 - 6.9;
80%
1360187-62-7

BrH*C4H8BrNO2

A

2-aminoacrylic acid methyl ester

B

68-41-7

cycloserine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In methanol; water at 0 - 20℃; for 5h;A 66%
B 27%
With hydroxylamine hydrochloride; sodium methylate In methanol; water at 0 - 20℃; for 9h;A 39%
B 48%
72270-01-0

D-cycloserine-L-tartrate

68-41-7

cycloserine

Conditions
ConditionsYield
With Amberlite IR-120 PLUS ion exchange resin (sodium form) In water Inert atmosphere;65%
121362-14-9

D-2-amino-3-chloropropionic acid chloride hydrochloride

68-41-7

cycloserine

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In water; toluene at -5 - 30℃; pH=11 - 12; pH-value;58.1%
120883-74-1

D-2-amino-3-chloropropionohydroxamic acid hydrochloride

68-41-7

cycloserine

Conditions
ConditionsYield
With sodium hydroxide In water at 25℃; pH=11; Cooling;50%
23628-35-5

3-chloro-D-alanine hydroxyamide

68-41-7

cycloserine

Conditions
ConditionsYield
With water; triethylamine
Downstream Products
312-84-5
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    D-Cycloserine

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  • D-Cycloserine cas 68-41-7

  • Casno:

    68-41-7

    D-Cycloserine cas 68-41-7

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  • CYCLOSERINE

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    68-41-7

    CYCLOSERINE

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  • D-Cycloserine

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    68-41-7

    D-Cycloserine

    Min.Order: 1 Gram

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  • D-Cycloserine Manufacturer

  • Casno:

    68-41-7

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    Min.Order: 10 Gram

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  • D-Cycloserine

  • Casno:

    68-41-7

    D-Cycloserine

    Min.Order: 1 Gram

    FOB Price:  USD $ 0.0-0.0

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  • D-Cycloserine

  • Casno:

    68-41-7

    D-Cycloserine

    Min.Order: 100 Gram

    FOB Price:  USD $ 100.0-2000.0

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Consensus Reports

EPA Genetic Toxicology Program.

Specification

The Cycloserine, with the CAS registry number 68-41-7 and EINECS registry number 200-688-4, has the systematic name of (4R)-4-amino-1,2-oxazolidin-3-one. It is a kind of white to pale crystal powder, and belongs to the following product categories: Variousamine; Miscellaneous Biochemicals; Chiral; Amines (Chiral); Chiral Building Blocks; Synthetic Organic Chemistry; Amino Acids; Glutamate receptor; Glutamate; Antibiotics. And the molecular formula of this chemical is C3H6N2O2. What's more, it should be stored at -20°C.

The physical properties of Cycloserine are as followings: (1)ACD/LogP: -2.988; (2)ACD/LogD (pH 5.5): -3.54; (3)ACD/LogD (pH 7.4): -3.00; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 4; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.475; (12)Molar Refractivity: 22.472 cm3; (13)Molar Volume: 79.861 cm3; (14)Polarizability: 8.909 10-24cm3; (15)Surface Tension: 40.8849983215332 dyne/cm; (16)Density: 1.278 g/cm3

Preparation of Cycloserine: It can be synthesised by fomentation and direct synthesis technique. Fomentation need zymogen the Actinomyces laven-dulae, and the fermentation medium dextrin, glucose, starch, soybean powder, yeast powder, ammonium sulfate, ammonium nitrate, calcium carbonate, sodium chloride, magnesium sulfate, soybean oil and so on. Direct synthesis technique is a cyclization reaction between β-amino alanine ethyl ester dihydrochloride oxygen and KOH.

Uses of Cycloserine: It is an antibiotic effective against Mycobacterium tuberculosis, and usually used for the treatment of tuberculosis. It is also being trialed as an adjuvant to exposure therapy for anxiety disorders. 

You should be cautious while dealing with this chemical. Heating may cause an explosion, and it is also harmful by inhalation. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and avoid contacting with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1NOC[C@H]1N
(2)InChI: InChI=1/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
(3)InChIKey: DYDCUQKUCUHJBH-UWTATZPHBN

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 2gm/kg (2000mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956.
dog LDLo subcutaneous 2gm/kg (2000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

GASTROINTESTINAL: NAUSEA OR VOMITING
Antibiotics and Chemotherapy Vol. 6, Pg. 708, 1956.
guinea pig LD50 oral > 2gm/kg (2000mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956.
guinea pig LD50 subcutaneous > 1gm/kg (1000mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956.
human TDLo oral 560mg/kg/4W-I (560mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: WAKEFULNESS
Diseases of the Chest. Vol. 29, Pg. 241, 1956.
man TDLo unreported 64mg/kg/4D-I (64mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SLEEP
Antibiotics Annual. Vol. 3, Pg. 148, 1955/1956.
monkey LDLo subcutaneous 4gm/kg (4000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: ATAXIA
Antibiotics and Chemotherapy Vol. 6, Pg. 708, 1956.
mouse LD50 intraperitoneal 180mg/kg (180mg/kg)   "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 238, 1967.
mouse LD50 intravenous 560mg/kg (560mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 1085, 1980.
mouse LD50 oral 5290mg/kg (5290mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956.
mouse LD50 subcutaneous 1400mg/kg (1400mg/kg)   Yakkyoku. Pharmacy. Vol. 31, Pg. 1085, 1980.
rabbit LD oral > 2gm/kg (2000mg/kg)   Antibiotics and Chemotherapy Vol. 6, Pg. 382, 1956.
rat LD50 oral > 5gm/kg (5000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956.
rat LD50 subcutaneous > 3gm/kg (3000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Antibiotics and Chemotherapy Vol. 6, Pg. 360, 1956.
women TDLo oral 60mg/kg (60mg/kg) BEHAVIORAL: COMA British Medical Journal. Vol. 1, Pg. 907, 1965.
women TDLo oral 5gm/kg/71W-I (5000mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES
Rinsho Shinkeigaku. Clinical Neurology. Vol. 7, Pg. 357, 1967.
women TDLo unreported 40mg/kg/2D-I (40mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Tubercle. Vol. 38, Pg. 297, 1957.

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