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procainamide

Names

[ CAS No. ]:
51-06-9

[ Name ]:
procainamide

[Synonym ]:
4-Amino-N-(2-diethylaminoethyl)benzamide
4-amino-N-[2-(diethylamino)ethyl]benzamide

Biological Activity

[Description]:

Procainamide is a specific and potent inhibitor of DNA methyltransferase 1 (DNMT1). Procainamide is a Class 1A antiarrhythmic agent. Procainamide has the potential for the research of cancer and arrhythmias[1][2].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Cardiovascular Disease
Signaling Pathways >> Epigenetics >> DNA Methyltransferase

[Target]

DNMT1[1]


[References]

[1]. Lee BH, et al. Procainamide is a specific inhibitor of DNA methyltransferase 1. J Biol Chem. 2005;280(49):40749-40756.

[2]. Pritchard B, et al. Procainamide. [Updated 2021 Aug 8]. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2022 Jan-.

Chemical & Physical Properties

[ Density]:
1.06

[ Boiling Point ]:
421.8ºC at 760mmHg

[ Melting Point ]:
47°C

[ Molecular Formula ]:
C13H21N3O

[ Molecular Weight ]:
235.32500

[ Flash Point ]:
208.9ºC

[ Exact Mass ]:
235.16800

[ PSA ]:
58.36000

[ LogP ]:
2.31250

[ Index of Refraction ]:
1.5700 (estimate)

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
CV2275000
CHEMICAL NAME :
Benzamide, p-amino-N-(2-(diethylamino)ethyl)-
CAS REGISTRY NUMBER :
51-06-9
BEILSTEIN REFERENCE NO. :
2214285
LAST UPDATED :
199612
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C13-H21-N3-O
MOLECULAR WEIGHT :
235.37
WISWESSER LINE NOTATION :
ZR DVM2N2&2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
8579 mg/kg/43W-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - fibrosing alveolitis
REFERENCE :
AJMEAZ American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 76,146,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
29 mg/kg
TOXIC EFFECTS :
Behavioral - tremor
REFERENCE :
AJCDAG American Journal of Cardiology. (Technical Pub. Co., 875 Third Ave., New York, NY 10022) V.1- 1958- Volume(issue)/page/year: 57,340,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1826 mg/kg/13W-I
TOXIC EFFECTS :
Cardiac - other changes
REFERENCE :
AHJOA2 American Heart Journal. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1925- Volume(issue)/page/year: 83,798,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
2280 mg/kg/22W
TOXIC EFFECTS :
Musculoskeletal - joints
REFERENCE :
BHJUAV British Heart Journal. (British Medical Journal, Box 560B, Kennebunkport, ME 04046) V.1- 1939- Volume(issue)/page/year: 34,284,1972
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
583 mg/kg/12D-C
TOXIC EFFECTS :
Cardiac - arrhythmias (including changes in conduction)
REFERENCE :
AHJOA2 American Heart Journal. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1925- Volume(issue)/page/year: 109,375,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1950 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CCCCAK Collection of Czechoslovak Chemical Communications. (Academic Press Inc. Ltd., 24-28 Oval Rd., London NW1 7DX, UK) V.1- 1929- Volume(issue)/page/year: 42,3628,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
110 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPTOAN Russian Pharmacology and Toxicology (English Translation). Translation of FATOAO. (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey, UK) V.30- 1967- Volume(issue)/page/year: 33,292,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
110 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 54(3),32,1991
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
525 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CCCCAK Collection of Czechoslovak Chemical Communications. (Academic Press Inc. Ltd., 24-28 Oval Rd., London NW1 7DX, UK) V.1- 1929- Volume(issue)/page/year: 42,3628,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
178 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia
REFERENCE :
PJPPAA Polish Journal of Pharmacology and Pharmacy. (ARS Polona, POB 1001, 00-068 Warsaw 1, Poland) V.25- 1973- Volume(issue)/page/year: 37,551,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
720 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia
REFERENCE :
PJPPAA Polish Journal of Pharmacology and Pharmacy. (ARS Polona, POB 1001, 00-068 Warsaw 1, Poland) V.25- 1973- Volume(issue)/page/year: 37,551,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
49 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia
REFERENCE :
PJPPAA Polish Journal of Pharmacology and Pharmacy. (ARS Polona, POB 1001, 00-068 Warsaw 1, Poland) V.25- 1973- Volume(issue)/page/year: 37,551,1985
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2210 mg/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: 21,253,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
170 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PJPPAA Polish Journal of Pharmacology and Pharmacy. (ARS Polona, POB 1001, 00-068 Warsaw 1, Poland) V.25- 1973- Volume(issue)/page/year: 32,833,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
125 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PJPPAA Polish Journal of Pharmacology and Pharmacy. (ARS Polona, POB 1001, 00-068 Warsaw 1, Poland) V.25- 1973- Volume(issue)/page/year: 32,833,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
280 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 12,77,1957 *** REVIEWS *** TOXICOLOGY REVIEW INTEAG Internist. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) V.1- 1960- Volume(issue)/page/year: 15,7,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X4172 No. of Facilities: 66 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 8032 (estimated) No. of Female Employees: 7252 (estimated)

Safety Information

[ Hazard Codes ]:
T+

[ RIDADR ]:
2811

[ Packaging Group ]:

[ HS Code ]:
2924299090

Synthetic Route

Precursor & DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%


Related Compounds