Synonym
Nortriptyline, Allegron, Aventyl, Desitriptyline, Desmethylamitriptylin; Nortriptyline HCl; Lilly 38489; N 7048
IUPAC/Chemical Name
3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N-methylpropan-1-amine hydrochloride
InChi Key
SHAYBENGXDALFF-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H21N.ClH/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19;/h2-5,7-11,20H,6,12-14H2,1H3;1H
SMILES Code
CNCC/C=C1C2=CC=CC=C2CCC3=CC=CC=C3\1
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
1. Biber A, Durusu İZ, Özen C. In vitro anticancer effect of tricyclic antidepressant nortriptyline on multiple myeloma. Turk J Biol. 2018 Oct 25;42(5):414-421. doi: 10.3906/biy-1802-11. PMID: 30930625; PMCID: PMC6438120.
2. Shin SE, Li H, Kim HS, Kim HW, Seo MS, Ha KS, Han ET, Hong SH, Firth AL, Choi IW, Bae YM, Park WS. Nortriptyline, a tricyclic antidepressant, inhibits voltage-dependent K+ channels in coronary arterial smooth muscle cells. Korean J Physiol Pharmacol. 2017 Mar;21(2):225-232. doi: 10.4196/kjpp.2017.21.2.225. Epub 2017 Feb 21. PMID: 28280416; PMCID: PMC5343056.
3. Jeong JH, Kim DK, Lee NS, Jeong YG, Kim HW, Kim JS, Han SY. Neuroprotective Effect of Nortriptyline in Overt Hepatic Encephalopathy Through Attenuation of Mitochondrial Dysfunction. ASN Neuro. 2018 Jan-Dec;10:1759091418810583. doi: 10.1177/1759091418810583. PMID: 30428281; PMCID: PMC6238202.
4. Yuan SY, Cheng CL, Ho HC, Wang SS, Chiu KY, Su CK, Ou YC, Lin CC. Nortriptyline induces mitochondria and death receptor-mediated apoptosis in bladder cancer cells and inhibits bladder tumor growth in vivo. Eur J Pharmacol. 2015 Aug 15;761:309-20. doi: 10.1016/j.ejphar.2015.06.007. Epub 2015 Jun 15. PMID: 26086857.
In vitro activity:
1. Biber A, Durusu İZ, Özen C. In vitro anticancer effect of tricyclic antidepressant nortriptyline on multiple myeloma. Turk J Biol. 2018 Oct 25;42(5):414-421. doi: 10.3906/biy-1802-11. PMID: 30930625; PMCID: PMC6438120.
2. Shin SE, Li H, Kim HS, Kim HW, Seo MS, Ha KS, Han ET, Hong SH, Firth AL, Choi IW, Bae YM, Park WS. Nortriptyline, a tricyclic antidepressant, inhibits voltage-dependent K+ channels in coronary arterial smooth muscle cells. Korean J Physiol Pharmacol. 2017 Mar;21(2):225-232. doi: 10.4196/kjpp.2017.21.2.225. Epub 2017 Feb 21. PMID: 28280416; PMCID: PMC5343056.
In vivo activity:
1. Jeong JH, Kim DK, Lee NS, Jeong YG, Kim HW, Kim JS, Han SY. Neuroprotective Effect of Nortriptyline in Overt Hepatic Encephalopathy Through Attenuation of Mitochondrial Dysfunction. ASN Neuro. 2018 Jan-Dec;10:1759091418810583. doi: 10.1177/1759091418810583. PMID: 30428281; PMCID: PMC6238202.
2. Yuan SY, Cheng CL, Ho HC, Wang SS, Chiu KY, Su CK, Ou YC, Lin CC. Nortriptyline induces mitochondria and death receptor-mediated apoptosis in bladder cancer cells and inhibits bladder tumor growth in vivo. Eur J Pharmacol. 2015 Aug 15;761:309-20. doi: 10.1016/j.ejphar.2015.06.007. Epub 2015 Jun 15. PMID: 26086857.
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
30.0 |
100.00 |
| DMSO |
56.8 |
189.36 |
| Ethanol |
37.0 |
123.40 |
| PBS (pH 7.2) |
1.0 |
3.34 |
| Water |
33.1 |
110.29 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
299.84
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Biber A, Durusu İZ, Özen C. In vitro anticancer effect of tricyclic antidepressant nortriptyline on multiple myeloma. Turk J Biol. 2018 Oct 25;42(5):414-421. doi: 10.3906/biy-1802-11. PMID: 30930625; PMCID: PMC6438120.
2. Shin SE, Li H, Kim HS, Kim HW, Seo MS, Ha KS, Han ET, Hong SH, Firth AL, Choi IW, Bae YM, Park WS. Nortriptyline, a tricyclic antidepressant, inhibits voltage-dependent K+ channels in coronary arterial smooth muscle cells. Korean J Physiol Pharmacol. 2017 Mar;21(2):225-232. doi: 10.4196/kjpp.2017.21.2.225. Epub 2017 Feb 21. PMID: 28280416; PMCID: PMC5343056.
3. Jeong JH, Kim DK, Lee NS, Jeong YG, Kim HW, Kim JS, Han SY. Neuroprotective Effect of Nortriptyline in Overt Hepatic Encephalopathy Through Attenuation of Mitochondrial Dysfunction. ASN Neuro. 2018 Jan-Dec;10:1759091418810583. doi: 10.1177/1759091418810583. PMID: 30428281; PMCID: PMC6238202.
4. Yuan SY, Cheng CL, Ho HC, Wang SS, Chiu KY, Su CK, Ou YC, Lin CC. Nortriptyline induces mitochondria and death receptor-mediated apoptosis in bladder cancer cells and inhibits bladder tumor growth in vivo. Eur J Pharmacol. 2015 Aug 15;761:309-20. doi: 10.1016/j.ejphar.2015.06.007. Epub 2015 Jun 15. PMID: 26086857.
In vitro protocol:
1. Biber A, Durusu İZ, Özen C. In vitro anticancer effect of tricyclic antidepressant nortriptyline on multiple myeloma. Turk J Biol. 2018 Oct 25;42(5):414-421. doi: 10.3906/biy-1802-11. PMID: 30930625; PMCID: PMC6438120.
2. Shin SE, Li H, Kim HS, Kim HW, Seo MS, Ha KS, Han ET, Hong SH, Firth AL, Choi IW, Bae YM, Park WS. Nortriptyline, a tricyclic antidepressant, inhibits voltage-dependent K+ channels in coronary arterial smooth muscle cells. Korean J Physiol Pharmacol. 2017 Mar;21(2):225-232. doi: 10.4196/kjpp.2017.21.2.225. Epub 2017 Feb 21. PMID: 28280416; PMCID: PMC5343056.
In vivo protocol:
1. Jeong JH, Kim DK, Lee NS, Jeong YG, Kim HW, Kim JS, Han SY. Neuroprotective Effect of Nortriptyline in Overt Hepatic Encephalopathy Through Attenuation of Mitochondrial Dysfunction. ASN Neuro. 2018 Jan-Dec;10:1759091418810583. doi: 10.1177/1759091418810583. PMID: 30428281; PMCID: PMC6238202.
2. Yuan SY, Cheng CL, Ho HC, Wang SS, Chiu KY, Su CK, Ou YC, Lin CC. Nortriptyline induces mitochondria and death receptor-mediated apoptosis in bladder cancer cells and inhibits bladder tumor growth in vivo. Eur J Pharmacol. 2015 Aug 15;761:309-20. doi: 10.1016/j.ejphar.2015.06.007. Epub 2015 Jun 15. PMID: 26086857.
1: Derry S, Wiffen PJ, Aldington D, Moore RA. Nortriptyline for neuropathic pain in adults. Cochrane Database Syst Rev. 2015 Jan 8;1:CD011209. doi: 10.1002/14651858.CD011209.pub2. Review. PubMed PMID: 25569864.
2: Macaluso M, Preskorn SH. CYP 2D6 PM status and antidepressant response to nortriptyline and venlafaxine: is it more than just drug metabolism? J Clin Psychopharmacol. 2011 Apr;31(2):143-5. doi: 10.1097/JCP.0b013e318212d7cb. Review. PubMed PMID: 21346604.
3: Dhippayom T, Chaiyakunapruk N, Jongchansittho T. Safety of nortriptyline at equivalent therapeutic doses for smoking cessation: a systematic review and meta-analysis. Drug Saf. 2011 Mar 1;34(3):199-210. doi: 10.2165/11585950-000000000-00000. Review. PubMed PMID: 21332244.
4: Hughes JR, Stead LF, Lancaster T. Nortriptyline for smoking cessation: a review. Nicotine Tob Res. 2005 Aug;7(4):491-9. Review. PubMed PMID: 16085520.
5: Kragh-Søorensen P, Hansen CE, Baastrup PC. Relationship between antidepressant effect and plasma level of nortriptyline. Clinical studies. Pharmakopsychiatr Neuropsychopharmakol. 1976 Jan;9(1):27-32. Review. PubMed PMID: 790409.
6: Wagena EJ, Knipschild P, Zeegers MP. Should nortriptyline be used as a first-line aid to help smokers quit? Results from a systematic review and meta-analysis. Addiction. 2005 Mar;100(3):317-26. Review. PubMed PMID: 15733245.
7: Breyer-Pfaff U. The metabolic fate of amitriptyline, nortriptyline and amitriptylinoxide in man. Drug Metab Rev. 2004 Oct;36(3-4):723-46. Review. PubMed PMID: 15554244.
8: Yasuda K. [Tricyclic antidepressants (imipramine, desipramine, amitriptyline, nortriptyline)]. Nihon Rinsho. 1995 Feb;53 Su Pt 1:934-7. Review. Japanese. PubMed PMID: 8753592.
9: Nordin C, Bertilsson L. Active hydroxymetabolites of antidepressants. Emphasis on E-10-hydroxy-nortriptyline. Clin Pharmacokinet. 1995 Jan;28(1):26-40. Review. PubMed PMID: 7712660.
10: Rubin EH, Biggs JT, Preskorn SH. Nortriptyline pharmacokinetics and plasma levels: implications for clinical practice. J Clin Psychiatry. 1985 Oct;46(10):418-24. Review. PubMed PMID: 3900052.
11: Bonaccorsi A, Garattini S. Cardiac effects of nortriptyline and other tricyclic antidepressant drugs. Gen Pharmacol. 1978;9(2):81-4. Review. PubMed PMID: 350699.
