Dextroamphetamine

2D Structure

Generated by CDK Depict.

3D Structure

Visualised by LiteMol software.

Source:

General
Identifier	MM16720
SMILES	CC(N)Cc1ccccc1 Presented in the original dataset.
InChIKey	KWTSXDURSIMDCE-UHFFFAOYSA-N Automatically obtained from RDkit software.
MW [Da]	135.21 Automatically obtained from RDkit software.
LogP	1.58 Automatically obtained from RDkit software.

Links
PubChem	N/A
DrugBank	N/A
ChEBI	N/A
PDB	N/A
ChEMBL	N/A

Similar entries

P-chloroamphetamine

Similarity: 0.7313

Similarity to P-chloroamphetamine

Tanimoto metric	0.7313
Cosine metric	0.8551
Dice metric	0.8448

MW:

169.66

PI:

Total passive interactions

Dextroamphetamine	3
P-chloroamphetamine	1

LogP:

2.23

AI:

Total active interactions

Dextroamphetamine	6
P-chloroamphetamine	0

4-Phenylbutylamine

Similarity: 0.617

Similarity to 4-Phenylbutylamine

Tanimoto metric	0.617
Cosine metric	0.7634
Dice metric	0.7632

MW:

149.24

PI:

Total passive interactions

Dextroamphetamine	3
4-Phenylbutylamine	9

LogP:

1.97

AI:

Total active interactions

Dextroamphetamine	6
4-Phenylbutylamine	0

L-Phenylalanine

Similarity: 0.6158

Similarity to L-Phenylalanine

Tanimoto metric	0.6158
Cosine metric	0.7847
Dice metric	0.7622

MW:

165.19

PI:

Total passive interactions

Dextroamphetamine	3
L-Phenylalanine	13

LogP:

0.64

AI:

Total active interactions

Dextroamphetamine	6
L-Phenylalanine	1

+36 more

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Target	Uniprot ID	Type	pKm	pEC₅₀	pK_i	pIC₅₀	Primary reference	Secondary reference	Note
SLC6A2	P23975	Inhibitor			7		Tatsumi M, Groshan K, Blakely RD, Richelson E.: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol, Volume 340 (2-3), 1997 Tatsumi M, Groshan K, Blakely RD, Richelson E.: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol, Volume 340 (2-3), 1997	Harding SD, Armstrong JF, Faccenda E, Southan C, Alexander SPH, Davenport AP, Spedding M, Davies JA.: The IUPHAR/BPS Guide to PHARMACOLOGY in 2024. Nucleic Acids Res, Volume 52 (d1), D1438-D1449, 2024 Harding SD, Armstrong JF, Faccenda E, Southan C, Alexander SPH, Davenport AP, Spedding M, Davies JA.: The IUPHAR/BPS Guide to PHARMACOLOGY in 2024. Nucleic Acids Res, Volume 52 (d1), D1438-D1449, 2024
SLC6A3	Q01959	Inhibitor			7		Lapinsky DJ, Velagaleti R, Yarravarapu N, Liu Y, Huang Y, Surratt CK, Lever JR, Foster JD, Acharya R, Vaughan RA, Deutsch HM.: Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling. Bioorg Med Chem, Volume 19 (1), 2011 Lapinsky DJ, Velagaleti R, Yarravarapu N, Liu Y, Huang Y, Surratt CK, Lever JR, Foster JD, Acharya R, Vaughan RA, Deutsch HM.: Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling. Bioorg Med Chem, Volume 19 (1), 2011	Harding SD, Armstrong JF, Faccenda E, Southan C, Alexander SPH, Davenport AP, Spedding M, Davies JA.: The IUPHAR/BPS Guide to PHARMACOLOGY in 2024. Nucleic Acids Res, Volume 52 (d1), D1438-D1449, 2024 Harding SD, Armstrong JF, Faccenda E, Southan C, Alexander SPH, Davenport AP, Spedding M, Davies JA.: The IUPHAR/BPS Guide to PHARMACOLOGY in 2024. Nucleic Acids Res, Volume 52 (d1), D1438-D1449, 2024
SLC22A1	O15245	Non-inhibitor				3.69	Koepsell H, Lips K, Volk C.: Polyspecific organic cation transporters: structure, function, physiological roles, and biopharmaceutical implications. Pharm Res, Volume 24 (7), 2007 Koepsell H, Lips K, Volk C.: Polyspecific organic cation transporters: structure, function, physiological roles, and biopharmaceutical implications. Pharm Res, Volume 24 (7), 2007	Mak L, Marcus D, Howlett A, Yarova G, Duchateau G, Klaffke W, Bender A, Glen RC.: Metrabase: a cheminformatics and bioinformatics database for small molecule transporter data analysis and (Q)SAR modeling. J Cheminform, Volume 7, 31, 2015 Mak L, Marcus D, Howlett A, Yarova G, Duchateau G, Klaffke W, Bender A, Glen RC.: Metrabase: a cheminformatics and bioinformatics database for small molecule transporter data analysis and (Q)SAR modeling. J Cheminform, Volume 7, 31, 2015
SLC6A2	P23975	Substrate		8.15			Lewin AH, Miller GM, Gilmour B.: Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class. Bioorg Med Chem, Volume 19 (23), 2011 Lewin AH, Miller GM, Gilmour B.: Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class. Bioorg Med Chem, Volume 19 (23), 2011	Zdrazil B, Felix E, Hunter F, Manners EJ, Blackshaw J, Corbett S, de Veij M, Ioannidis H, Lopez DM, Mosquera JF, Magarinos MP, Bosc N, Arcila R, Kizilören T, Gaulton A, Bento AP, Adasme MF, Monecke P, Landrum GA, Leach AR.: The ChEMBL Database in 2023: a drug discovery platform spanning multiple bioactivity data types and time periods. Nucleic Acids Res, Volume 52 (d1), D1180-D1192, 2024 Zdrazil B, Felix E, Hunter F, Manners EJ, Blackshaw J, Corbett S, de Veij M, Ioannidis H, Lopez DM, Mosquera JF, Magarinos MP, Bosc N, Arcila R, Kizilören T, Gaulton A, Bento AP, Adasme MF, Monecke P, Landrum GA, Leach AR.: The ChEMBL Database in 2023: a drug discovery platform spanning multiple bioactivity data types and time periods. Nucleic Acids Res, Volume 52 (d1), D1180-D1192, 2024
SLC6A2	P23975	Inhibitor				6.2	Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S.: An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'. Bioorg Med Chem Lett, Volume 23 (11), 2013 Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S.: An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'. Bioorg Med Chem Lett, Volume 23 (11), 2013	Zdrazil B, Felix E, Hunter F, Manners EJ, Blackshaw J, Corbett S, de Veij M, Ioannidis H, Lopez DM, Mosquera JF, Magarinos MP, Bosc N, Arcila R, Kizilören T, Gaulton A, Bento AP, Adasme MF, Monecke P, Landrum GA, Leach AR.: The ChEMBL Database in 2023: a drug discovery platform spanning multiple bioactivity data types and time periods. Nucleic Acids Res, Volume 52 (d1), D1180-D1192, 2024 Zdrazil B, Felix E, Hunter F, Manners EJ, Blackshaw J, Corbett S, de Veij M, Ioannidis H, Lopez DM, Mosquera JF, Magarinos MP, Bosc N, Arcila R, Kizilören T, Gaulton A, Bento AP, Adasme MF, Monecke P, Landrum GA, Leach AR.: The ChEMBL Database in 2023: a drug discovery platform spanning multiple bioactivity data types and time periods. Nucleic Acids Res, Volume 52 (d1), D1180-D1192, 2024
SLC6A4	P31645	Non-inhibitor				4.78	Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S.: An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'. Bioorg Med Chem Lett, Volume 23 (11), 2013 Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S.: An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'. Bioorg Med Chem Lett, Volume 23 (11), 2013	Zdrazil B, Felix E, Hunter F, Manners EJ, Blackshaw J, Corbett S, de Veij M, Ioannidis H, Lopez DM, Mosquera JF, Magarinos MP, Bosc N, Arcila R, Kizilören T, Gaulton A, Bento AP, Adasme MF, Monecke P, Landrum GA, Leach AR.: The ChEMBL Database in 2023: a drug discovery platform spanning multiple bioactivity data types and time periods. Nucleic Acids Res, Volume 52 (d1), D1180-D1192, 2024 Zdrazil B, Felix E, Hunter F, Manners EJ, Blackshaw J, Corbett S, de Veij M, Ioannidis H, Lopez DM, Mosquera JF, Magarinos MP, Bosc N, Arcila R, Kizilören T, Gaulton A, Bento AP, Adasme MF, Monecke P, Landrum GA, Leach AR.: The ChEMBL Database in 2023: a drug discovery platform spanning multiple bioactivity data types and time periods. Nucleic Acids Res, Volume 52 (d1), D1180-D1192, 2024

Hide empty columns:

Target

Uniprot ID

Type

pKm

pEC₅₀

pK_i

pIC₅₀

Primary
reference

Secondary
reference

Note

SLC6A2

P23975

Inhibitor

Tatsumi M, Groshan K, Blakely RD, Richelson E.: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol, Volume 340 (2-3), 1997

Harding SD, Armstrong JF, Faccenda E, Southan C, Alexander SPH, Davenport AP, Spedding M, Davies JA.: The IUPHAR/BPS Guide to PHARMACOLOGY in 2024. Nucleic Acids Res, Volume 52 (d1), D1438-D1449, 2024

SLC6A3

Q01959

Inhibitor

Lapinsky DJ, Velagaleti R, Yarravarapu N, Liu Y, Huang Y, Surratt CK, Lever JR, Foster JD, Acharya R, Vaughan RA, Deutsch HM.: Azido-iodo-N-benzyl derivatives of threo-methylphenidate (Ritalin, Concerta): Rational design, synthesis, pharmacological evaluation, and dopamine transporter photoaffinity labeling. Bioorg Med Chem, Volume 19 (1), 2011

SLC22A1

O15245

Non-inhibitor

3.69

Koepsell H, Lips K, Volk C.: Polyspecific organic cation transporters: structure, function, physiological roles, and biopharmaceutical implications. Pharm Res, Volume 24 (7), 2007

Mak L, Marcus D, Howlett A, Yarova G, Duchateau G, Klaffke W, Bender A, Glen RC.: Metrabase: a cheminformatics and bioinformatics database for small molecule transporter data analysis and (Q)SAR modeling. J Cheminform, Volume 7, 31, 2015

SLC6A2

P23975

Substrate

8.15

Lewin AH, Miller GM, Gilmour B.: Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class. Bioorg Med Chem, Volume 19 (23), 2011

Zdrazil B, Felix E, Hunter F, Manners EJ, Blackshaw J, Corbett S, de Veij M, Ioannidis H, Lopez DM, Mosquera JF, Magarinos MP, Bosc N, Arcila R, Kizilören T, Gaulton A, Bento AP, Adasme MF, Monecke P, Landrum GA, Leach AR.: The ChEMBL Database in 2023: a drug discovery platform spanning multiple bioactivity data types and time periods. Nucleic Acids Res, Volume 52 (d1), D1180-D1192, 2024

SLC6A2

P23975

Inhibitor

6.2

Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S.: An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'. Bioorg Med Chem Lett, Volume 23 (11), 2013

SLC6A4

P31645

Non-inhibitor

4.78

Methods