protriptyline

Modify Date: 2024-01-09 17:02:37

protriptyline Structure
protriptyline structure
Common Name protriptyline
CAS Number 438-60-8 Molecular Weight 263.37700
Density 1.026 g/cm3 Boiling Point 407.7ºC at 760 mmHg
Molecular Formula C19H21N Melting Point N/A
MSDS N/A Flash Point 198.3ºC

 Use of protriptyline


Protriptyline is a potent antidepressant agent. Protriptyline inhibits AChE activity with IC50 value of 0.06 mM and inhibits Aβ Self-Assembly. Protriptyline can be used for depression and Alzheimers disease[1][2][3].

 Names

Name protriptyline
Synonym More Synonyms

 protriptyline Biological Activity

Description Protriptyline is a potent antidepressant agent. Protriptyline inhibits AChE activity with IC50 value of 0.06 mM and inhibits Aβ Self-Assembly. Protriptyline can be used for depression and Alzheimers disease[1][2][3].
Related Catalog
In Vitro Protriptyline (0-70 μM; 24 hours; PC3 cells) causes cytotoxicity in PC3 cells[2]. Cell Cytotoxicity Assay[2] Cell Line: PC3 cells Concentration: 50, 60 and 70 μM Incubation Time: 24 hours Result: Decreased cell viability in a concentration-dependent manner.
In Vivo Protriptyline (10 mg/kg; i.p.; for 21 days; rat model of AD) improves spatial learning and retention memory in STZ treated rats[3]. Animal Model: Rat model of AD[3] Dosage: 10 mg/kg Administration: Intraperitoneal injection; for 21 days. Result: Reduced pTau, Aβ42 and BACE-1 levels, neurodegeneration, oxidative stress and glial activation. Improved p-ERK/ERK ratio and enhanced BDNF and CREB levels by reducing NFκB and GFAP expression.
References

[1]. Bansode SB, et, al. Molecular investigations of protriptyline as a multi-target directed ligand in Alzheimer's disease. PLoS One. 2014 Aug 20;9(8):e105196.

[2]. Chang HT, et, al. The mechanism of protriptyline-induced Ca2+ movement and non-Ca2+-triggered cell death in PC3 human prostate cancer cells. J Recept Signal Transduct Res. 2015;35(5):429-34.

[3]. Tiwari V, et, al. Protriptyline improves spatial memory and reduces oxidative damage by regulating NFκB-BDNF/CREB signaling axis in streptozotocin-induced rat model of Alzheimer's disease. Brain Res. 2021 Mar 1;1754:147261.

 Chemical & Physical Properties

Density 1.026 g/cm3
Boiling Point 407.7ºC at 760 mmHg
Molecular Formula C19H21N
Molecular Weight 263.37700
Flash Point 198.3ºC
Exact Mass 263.16700
PSA 12.03000
LogP 4.69280

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HP1050000
CHEMICAL NAME :
5H-Dibenzo(a,d)cycloheptene-5-propylamine, N-methyl-
CAS REGISTRY NUMBER :
438-60-8
LAST UPDATED :
199612
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C19-H21-N
MOLECULAR WEIGHT :
263.41
WISWESSER LINE NOTATION :
L C676 BHJ B3M1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
240 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPPAO Farmaco, Edizione Pratica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 25,519,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
42 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPPAO Farmaco, Edizione Pratica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 25,519,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
269 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPPAO Farmaco, Edizione Pratica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 25,519,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
67 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPPAO Farmaco, Edizione Pratica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 25,519,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
192 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPPAO Farmaco, Edizione Pratica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 25,519,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
30 mg/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay)
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 17,65,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
310 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPPAO Farmaco, Edizione Pratica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 25,519,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
8200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPPAO Farmaco, Edizione Pratica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 25,519,1970 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
630 mg/kg/6W-I
TOXIC EFFECTS :
Cardiac - EKG changes not diagnostic of specified effects Cardiac - pulse rate increase, without fall in BP
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,1709,1980 *** REVIEWS *** TOXICOLOGY REVIEW IDPYAK Industrial Pharmacology. (Mount Kisco, NY) V.1-3, 1974-79. Discontinued. Volume(issue)/page/year: 2,209,1975

 Safety Information

HS Code 2921499090

 Synthetic Route

~%

protriptyline Structure

protriptyline

CAS#:438-60-8

Literature: Apicore, LLC Patent: US2008/139848 A1, 2008 ; Location in patent: Page/Page column 3 ;

~%

protriptyline Structure

protriptyline

CAS#:438-60-8

Literature: Engelhardt,E.L. et al. Journal of Medicinal Chemistry, 1968 , vol. 11, # 2 p. 325 - 332

~%

protriptyline Structure

protriptyline

CAS#:438-60-8

Literature: Gribble,G.W. et al. Synthesis, 1977 , p. 172 - 176

~%

protriptyline Structure

protriptyline

CAS#:438-60-8

Literature: Engelhardt,E.L. et al. Journal of Medicinal Chemistry, 1968 , vol. 11, # 2 p. 325 - 332

 Customs

HS Code 2921499090
Summary 2921499090 other aromatic monoamines and their derivatives; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

 Synonyms

N-Methyl-5H-dibenzo[a,d]cycloheptene-5-propylamine
5-(3-Methylaminopropyl)-5H-Dibenzo[a,d]cycloheptene
DIBENZO(A,D)CYCLOHEPTENE-5-PROPYLAMINE,N-METHYL
Amimetilina
5H-Dibenzo[a,d]cycloheptene-5-propylamine,N-methyl
Triptil
N-methyl-5H-dibenzo(a,d)cycloheptene-5-propanamine
Protriptylin
Protryptyline
3-(dibenzo(a,d)cyclohepten-5-yl)propylmethylamine
proptriptyline
Vivactil
PROTRIPTYLINE
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