Nortriptyline

Details

• Internal ID: e736713e-e8b2-489f-baae-264b3f2d3b63
• Taxonomy: Benzenoids > Dibenzocycloheptenes
• IUPAC Name: N-methyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine
• SMILES (Canonical): CNCCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
• SMILES (Isomeric): CNCCC=C1C2=CC=CC=C2CCC3=CC=CC=C31
• InChI: InChI=1S/C19H21N/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
• InChI Key: PHVGLTMQBUFIQQ-UHFFFAOYSA-N
• Popularity: 8,184 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁N
• Molecular Weight: 263.40 g/mol
• Exact Mass: 263.167399674 g/mol
• Topological Polar Surface Area (TPSA): 12.00 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 3.83
• H-Bond Acceptor: 1
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• Aventyl
• 72-69-5
• Desitriptilina
• Noramitriptyline
• Lumbeck
• Desmethylamitriptyline
• Noritren
• Sensaval
• Ateben
• Avantyl
• Demethylamitriptyline
• Sesaval
• Pamelor
• Nortryptiline
• Nortryptyline
• Demethylamitryptyline
• Nortrilen
• Nortriptylinum
• Amitryptyline, demethyl-
• Psychostyl
• Allegron
• Desitriptyline
• Nortriptilina
• Nortriptilina [DCIT]
• Nortriptyline [INN:BAN]
• Demethylamitriptylene
• Desmethylamitriptylin
• Acetexa
• Altilev
• Vividyl
• Nortriptylinum [INN-Latin]
• Nortrilen (TN)
• Pamelor hydrochloride
• 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N-methyl-
• CCRIS 9175
• Aventyl;Desitriptilina
• Nortriptyline (INN)
• 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
• EINECS 200-788-8
• UNII-BL03SY4LXB
• Nortriptylene hydrochloride
• BL03SY4LXB
• NSC-757234
• BRN 2216786
• AVENTYL HCL
• 5-(3-Methylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene
• CHEBI:7640
• 5-(3-(Methylamino)propylidene)dibenzo(a,e)cyclohepta(1,5)diene
• 5-(alpha-Methylaminopropylidene)dibenzo(a,d)cyclohepta(1,4)diene
• demethylamitriptylin
• N-Methyl-3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-yliden)propylamin
• 10,11-Dihydro-5-(3-methylaminopropylidene)-5H-dibenzo(a,d)(1,4)cycloheptene
• 10,11-Dihydro-N-methyl-5H-dibenzo(a,d)cycloheptene-delta(5,gamma)-propylamine
• 3-(10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N-methylpropylamine
• 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N-methylpropan-1-amine
• NCI169453
• 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-
• NCI-169453
• HSDB 3371
• Pamelor (TN)
• NSC169453
• NORTRIPTYLINE [INN]
• 5H-Dibenzo(a,d)cycloheptene-delta(sup 5),gamma-propylamine, 10,11-dihydro-N-methyl-
• Sensival Ventyl
• (2)10,11-Dihydro-N-methyl-5H-dibenzo[a,d]cycloheptene-.delta.5.gamma.-propylamine
• 10,11-dihydro-N-methyl-5H-dibenzo[a,d]cycloheptene-Delta(5,gamma)-propylamine
• N-methyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine
• NSC78248
• CAS-894-71-3
• nortriptylina
• nortriptylin-
• 5-[3-(Methylamino)propylidene]dibenzo[a,E]cyclohepta[1,5]diene
• Triptyline-M nor
• 10,11-Dihydro-5-(3-methylaminopropylidene)-5H-dibenzo[a,d][1,4]cycloheptene
• 3-(10,11-DIHYDRO-5H-DIBENZO(A,D)(7)ANNULEN-5-YLIDENE)-N-METHYLPROPAN-1-AMINE
• 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methylpropylamine
• Allegron (TN)
• Norpress (TN)
• Sensoval (TN)
• Aventyl (TN)
• Spectrum_001041
• Psychostyl (Salt/Mix)
• Prestwick0_000254
• Prestwick1_000254
• Prestwick2_000254
• Prestwick3_000254
• Spectrum2_000997
• Spectrum3_000526
• Spectrum4_000455
• Spectrum5_001377
• Lopac-N-7261
• NORTRIPTYLINE [MI]
• CHEMBL445
• D04WFD
• NCIStruc1_000856
• NCIStruc2_000700
• NCIOpen2_004361
• BIDD:PXR0187
• Lopac0_000868
• SCHEMBL34527
• BSPBio_000068
• BSPBio_002111
• KBioGR_000870
• KBioSS_001521
• NORTRIPTYLINE [VANDF]
• DivK1c_000151
• SPECTRUM1500442
• SPBio_001093
• SPBio_002287
• NORTRIPTYLINE [WHO-DD]
• BPBio1_000076
• GTPL2404
• DTXSID9023384
• HMS500H13
• KBio1_000151
• KBio2_001521
• KBio2_004089
• KBio2_006657
• KBio3_001611
• NINDS_000151
• PHVGLTMQBUFIQQ-UHFFFAOYSA-N
• BDBM112777
• HMS1920B20
• HMS2091J20
• KUC112478N
• Pharmakon1600-01500442
• CCG-38266
• NCGC00014483
• NSC757234
• PDSP1_001805
• PDSP2_001788
• CS-O-01980
• DB00540
• NCI 169453
• NSC 757234
• SDCCGSBI-0050843.P006
• IDI1_000151
• MRF-0000480
• QTL1_000063
• NCGC00014483-02
• NCGC00014483-03
• NCGC00014483-04
• NCGC00014483-05
• NCGC00014483-06
• NCGC00014483-07
• NCGC00014483-08
• NCGC00014483-09
• NCGC00014483-10
• NCGC00014483-11
• NCGC00014483-12
• NCGC00014483-14
• NCGC00014483-16
• NCGC00014483-23
• NCGC00024261-03
• NCGC00024261-04
• NCGC00024261-05
• NCGC00024261-06
• KSC-315-028-
• LS-60753
• methyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
• MS-23718
• NCI60_001354
• SBI-0050843.P004
• US8629135, SW-02
• HY-118620
• AB00052061
• CS-0067638
• EN300-57709
• C07274
• D08288
• F82279
• Q61387
• AB00052061_16
• SR-01000000223-4
• BRD-K91263825-003-03-2
• AMITRIPTYLINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
• 5-[3-(Methylamino)propylidene]dibenzo[a e]cyclohepta[1 5]diene
• 10 11-Dihydro-N-methyl-5H-dibenzo[a d]cycloheptane-Delta gamma propylamine
• 10,11-dihidro-N-metil-5H-dibenzo [a, d]-Cicloheptano .gamma.propilamina
• 1011-Dihydro-5-(3-methylaminopropylidene)-5H-dibenzo[ad][14]cycloheptene
• 5-(3-Methylaminopropylidene)-10 11-dihydro-5H-dibenzo[a d]cycloheptene
• '3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N-methylpropan-1-amine'
• 1-propanamina, 3-(10,11-dihidro-5h-dibenzo [a, d] ciclohepteno-5-ilideno)-n-metil-
• 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[ a,d]cyclohepten-5-ylidene)-N-methyl-
• 10 11-Dihydro-N-methyl-5H-dibenzo[a d]cycloheptene-Delta 5 gamma-propylamine
• 10,11-dihidro-5-(3-metilaminopropilidene)-5H-dibenzo [ a, d] [1,4] ciclohepteno
• 10,11-Dihydro-N-methyl-5H-dibenzo(a,d)cycloheptane-.DELTA.,.gamma.-propylamine
• 10,11-DIHYDRO-N-METHYL-5H-DIBENZO(A,D)CYCLOHEPTENE-D(SUP5,.GAMMA.)-PROPYLAMINE
• 10,11-dihydro-N-methyl-5H-dibenzo[a,d]cycloheptene-delta-5,gamma-propylamine
• 10,11-dihydro-N-methyl-5H-dibenzo[a,d]cycloheptene-Delta5,gamma-propylamine
• 3-(10 11-Dihydro-5H-dibenzo[a d]cyclohepten-5-ylidene)-N-methylpropylamine
• 3-(5,6-dihydrodibenzo[[?],[?]][7]annulen-11-ylidene)-N-methyl-propan-1-amine
• 5H-dibenzo [a, d] ciclohepteno-5,.Gamma.-propilamina,10,11-dihidro-N-metil-
• 5H-Dibenzo[a,d]cycloheptene-.DELTA.5,.gamma.-propylamine, 10,11-dihydro-N-methyl-
• 5H-Dibenzo[ad]cycloheptene-Delta 5gamma-propylamine1011-dihydro-N-methyl-(8CI)
• 21B
• methyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene]propyl})amine
• methyl(3-{tricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-2-ylidene}propyl)amine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9947	99.47%
Caco-2	+	0.9406	94.06%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	+	0.9714	97.14%
Subcellular localzation	Lysosomes	0.8521	85.21%
OATP2B1 inhibitior	-	0.8854	88.54%
OATP1B1 inhibitior	+	0.9369	93.69%
OATP1B3 inhibitior	+	0.9467	94.67%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.9000	90.00%
BSEP inhibitior	+	0.8594	85.94%
P-glycoprotein inhibitior	+	0.6050	60.50%
P-glycoprotein substrate	-	0.7548	75.48%
CYP3A4 substrate	+	0.5857	58.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6766	67.66%
CYP3A4 inhibition	-	0.7665	76.65%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	+	0.8932	89.32%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.9375	93.75%
CYP inhibitory promiscuity	-	0.5194	51.94%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.7865	78.65%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.5325	53.25%
Skin corrosion	-	0.6365	63.65%
Ames mutagenesis	-	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7128	71.28%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.5928	59.28%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.5444	54.44%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.5843	58.43%
Acute Oral Toxicity (c)	III	0.8000	80.00%
Estrogen receptor binding	+	0.6650	66.50%
Androgen receptor binding	+	0.7438	74.38%
Thyroid receptor binding	+	0.7195	71.95%
Glucocorticoid receptor binding	-	0.6015	60.15%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8450	84.50%
Honey bee toxicity	-	0.9381	93.81%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9456	94.56%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL223	P25100	Alpha-1d adrenergic receptor	273 nM	IC50	via CMAUP
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	732 nM	IC50	via CMAUP
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	94 nM	IC50	via CMAUP
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	203 nM	IC50	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3356	P05177	Cytochrome P450 1A2	25118.86 nM; 7943.28 nM	AC50; AC50	via CMAUP; via CMAUP
CHEMBL3622	P33261	Cytochrome P450 2C19	3000 nM	IC50	via CMAUP
CHEMBL3721	P10632	Cytochrome P450 2C8	49900 nM	Ki	PMID: 16248836
CHEMBL289	P10635	Cytochrome P450 2D6	2600 nM; 2300 nM	IC50; IC50	PMID: 15481972; PMID: 12502361
CHEMBL340	P08684	Cytochrome P450 3A4	12589.3 nM; 15848.9 nM; 12589.3 nM; 15848.9 nM	Potency; Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP; via CMAUP
CHEMBL2056	P21728	Dopamine D1 receptor	539 nM	IC50	via CMAUP
CHEMBL234	P35462	Dopamine D3 receptor	179 nM	IC50	via CMAUP
CHEMBL238	Q01959	Dopamine transporter	1678 nM	IC50	via CMAUP
CHEMBL231	P35367	Histamine H1 receptor	50 nM	IC50	via CMAUP
CHEMBL1941	P25021	Histamine H2 receptor	2334 nM	IC50	via CMAUP
CHEMBL5514	P42858	Huntingtin	25118.9 nM	Potency	via CMAUP
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82 nM	IC50	via CMAUP
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	347 nM	IC50	via CMAUP
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	171 nM	IC50	via CMAUP
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	95 nM	IC50	via CMAUP
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	27 nM	IC50	via CMAUP
CHEMBL222	P23975	Norepinephrine transporter	3.21 nM	IC50	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	35.5 nM; 35.5 nM; 251.2 nM	Potency; Potency; Potency	via Super-PRED; via CMAUP; via CMAUP
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	23280.9 nM; 23280.9 nM; 23280.9 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via CMAUP
CHEMBL224	P28223	Serotonin 2a (5-HT2a) receptor	51 nM	IC50	via CMAUP
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	136 nM	IC50	via CMAUP
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	16 nM	IC50	via CMAUP
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	554 nM; 214 nM	IC50; Ki	via CMAUP; via Super-PRED
CHEMBL228	P31645	Serotonin transporter	13 nM	IC50	via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	12589.3 nM; 12589.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	5000 nM; 1500 nM	IC50; IC50	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	94.97%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.02%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	91.66%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.07%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.05%	95.56%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.81%	95.83%
CHEMBL3401	O75469	Pregnane X receptor	82.31%	94.73%
CHEMBL222	P23975	Norepinephrine transporter	82.26%	96.06%
CHEMBL1841	P06241	Tyrosine-protein kinase FYN	82.18%	81.29%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.84%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.12%	99.17%

Plants that contains it

• Senegalia berlandieri
• Thymus quinquecostatus
• Thymus vulgaris

Cross-Links

• PubChem: 4543
• NPASS: NPC133162
• ChEMBL: CHEMBL445
• LOTUS: LTS0261727
• wikiData: Q61387