DL-amphetamine

pair of enantiomers

Class type of: amphetamines, 1-phenylpropan-2-amine alkaloid Q179452

Facts

23 properties

Instance of: group of stereoisomers
Subclass of: amphetamines, 1-phenylpropan-2-amine alkaloid
Part of: response to amphetamine, cellular response to amphetamine^[15]^[16]
Has use: medication^[17]
Active ingredient in: Evekeo, Adzenys, Dyanavel, Adderall, Benzedrine
Boiling point: +203^[29]
Canonical SMILES: CC(CC1=CC=CC=C1)N^[13]
Chemical formula: C₉H₁₃N^[14]
Defined daily dose: +15, +15
Density: +0.936^[26]
Described by source: Opium Law^[24]
Different from: D-methamphetamine^[25]
Found in taxon: Senegalia berlandieri^[18]
Legal status (medicine): boxed warning
Mass: +135.104799^[27]
Medical condition treated: attention deficit hyperactivity disorder, narcolepsy, obesity^[30]^[31]^[32]
Melting point: +11.3^[28]
P14834: Schedule I (Russia), Schedule I (Canada), Anlage III (Germany), Class B (United Kingdom), Schedule II (United States), Schedule II (Convention on Psychotropic Substances 1971)
Physically interacts with: Trace amine associated receptor 1, 5-hydroxytryptamine receptor 1A, solute carrier family 1 member 1, Solute carrier family 18 member A2, Flavin containing dimethylaniline monoxygenase 3, cytochrome P450 family 2 subfamily D member 6, dopamine beta-hydroxylase, Solute carrier family 6 member 2, solute carrier family 6 member 3^[4]^[5]^[6]^[7]^[8]^[9]^[10]^[11]^[12]
Pregnancy category: US pregnancy category C
Significant drug interaction: isocarboxazid, phenelzine, procarbazine, (±)-deprenyl, tranylcypromine^[19]^[20]^[21]^[22]^[23]
Subject has role: dopamine reuptake inhibitor, monoamine oxidase inhibitor, adrenergic uptake inhibitors, adrenergic agent, sympathomimetic drug, stimulant, dopaminergic, nootropic
World Health Organisation international non-proprietary name: amfetaminum, amfetamine, amfétamine, anfetamina, амфетамин, أمفيتامين, 苯丙胺^[33]^[34]^[35]^[36]^[37]^[38]^[39]

🏷️ Also known as

en β-aminopropylbenzene en β-phenylisopropylamine en whiz en uppers en α-methylphenethylamine en α-methylbenzeneethaneamine en rac-(2R)-1-phenylpropan-2-amine en louee en rac-amphetamine en speed en goey en DL-amphetamine en desoxynorephedrine en beta-Phenylisopropylamine en beta-phenylisopropylamin en (±)-amphetamine en amfetamine en alpha-methylphenylethylamine en amphetamine en beta-Aminopropylbenzene

🔖 Identifiers · 66

GND ID: 4122043-2
OpenAlex ID: C2777193897
ATC code: N06BA01
BNCF Thesaurus ID: 73149
BabelNet ID: 00003615n
CAMEO Chemicals ID: 4862
CAS Registry Number: 300-62-9, 60-15-1, 17108-96-2, 96332-84-2
ChEBI ID: 132233
ChEMBL ID: CHEMBL405
ChemSpider ID: 13852819
DSSTOX compound identifier: DTXCID402600
DSSTox substance ID: DTXSID4022600

Show all 66 identifiers +54

Dewey Decimal Classification: 616.9 (362.3–616.9, n=4)
DrugBank ID: DB00182
DrugCentral ID: 195
EC number: 206-096-2
ECHA Substance Infocard ID: 100.005.543
Encyclopædia Britannica Online ID: science/amphetamine
Encyclopædia Universalis ID: amphetamines
Freebase ID: /m/0_0j
Gmelin number: 406210
Google Knowledge Graph ID: /g/121xk39z
Gran Enciclopèdia Catalana ID: amfetamina
Gran Enciclopèdia Catalana ID (former scheme): 0077594
Guide to Pharmacology Ligand ID: 4804
HSDB ID: 3287
Human Metabolome Database ID: HMDB0014328
InChI: InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
InChIKey: KWTSXDURSIMDCE-UHFFFAOYSA-N
KBpedia ID: Amphetamine
KEGG ID: C07514
Lex ID: amfetamin
MassBank accession ID: MSBNK-Athens_Univ-AU154001, MSBNK-Athens_Univ-AU154002, MSBNK-Athens_Univ-AU154007, MSBNK-Athens_Univ-AU154008, MSBNK-Athens_Univ-AU154030, MSBNK-Eawag-EA282201, MSBNK-Eawag-EA282202, MSBNK-Eawag-EA282203, MSBNK-Eawag-EA282204, MSBNK-Eawag-EA282205, MSBNK-Eawag-EA282206, MSBNK-Eawag-EA282207, MSBNK-Eawag-EA282208, MSBNK-Eawag-EA282209, MSBNK-Eawag-EA282210, MSBNK-Eawag-EA282211, MSBNK-Eawag-EA282212, MSBNK-Eawag-EA282213, MSBNK-Eawag-EA282214, MSBNK-Waters-WA000407, MSBNK-Waters-WA000408, MSBNK-Waters-WA000409, MSBNK-Waters-WA000410
MeSH descriptor ID: D000661
MeSH tree code: D02.092.471.683.152.110
MedlinePlus drug identifier: a616004
Microsoft Academic ID (discontinued): 2777193897, 2910867446
NDF-RT ID: N0000147705
NDL Authority ID: 00560259
Namuwiki ID: 암페타민
OmegaWiki Defined Meaning: 804445
Probes And Drugs ID: PD010185
PubChem CID: 3007
Quora topic ID: Amphetamines
RationalWiki ID: Amphetamines
Reaxys registry number: 507867
RxNorm CUI: 725
Römpp online ID: RD-01-02214
SPLASH: splash10-014i-0900000000-8cb9815fcd67a6b46f05, splash10-014i-3900000000-5ec7b13e93ed8e0dc0b5, splash10-014u-3900000000-bbb73c900841d90c0ba1, splash10-0006-9400000000-074f0f58bee23b3ea45a, splash10-0006-9100000000-96e214b1c073232acc7e, splash10-0006-9000000000-b6e1299382e4b38f6c4f, splash10-0006-9000000000-2ed560c4c86538c3e790, splash10-0006-9000000000-6ddaf7d40e83a5c70c37, splash10-014u-3900000000-5a23e52436daebe58716, splash10-0006-9500000000-f28704987cc3eacc8917, splash10-0006-9100000000-421879391d3453649aad, splash10-0006-9000000000-f8b71db6439096bac2b0, splash10-0006-9000000000-270039c50b5f89d9c4ad, splash10-0006-9000000000-e84756122a0b431eee74, splash10-014i-3900000000-20cdadf7c5b742c53087, splash10-0006-9000000000-98cd0a725199f943d6cf
SureChEMBL ID: 8858
Topic's main category: Category:Amphetamine
Treccani ID: anfetamina
Treccani's Universo del corpo ID: anfetamine
UMLS CUI: C0002658
UNII: CK833KGX7E
UniChem compound ID: 612615
WikiProjectMed ID: Amphetamine
WikiSkripta article ID: 36942
WordNet 3.1 Synset ID: 02707012-n
World Health Organisation international non-proprietary name numeric ID: 377
YSA ID: Y112180
YSO ID: 5463
Yale LUX ID: concept/be9d6d81-dd7c-457f-8e2b-1082216c22aa
Yle topic ID: 18-218682
ZVG number: 490189
Ávvir topic ID: amfetamiidna

Report an error or request removal Lineage (PROV-JSON)

🔗 Connections

Subject has role 7

stimulant, monoamine oxidase inhibitor, sympathomimetic drug, nootropic, adrenergic uptake inhibitors, dopamine reuptake inhibitor, dopaminergic

Physically interacts with 5

cytochrome P450 family 2 subfamily D member 6, dopamine beta-hydroxylase, solute carrier family 6 member 3, 5-hydroxytryptamine receptor 1A, Solute carrier family 18 member A2

Significant drug interaction 4

procarbazine, phenelzine, tranylcypromine, isocarboxazid

Medical condition treated 3

obesity, attention deficit hyperactivity disorder, narcolepsy

Subtypes 2

dextroamphetamine, (R)-amphetamine

Active ingredient in 1

Adderall

Different from 1

D-methamphetamine

Found in taxon 1

Senegalia berlandieri

Has use 1

medication

Legal status (medicine) 1

boxed warning

Subclass of 1

amphetamines

Topic's main category 1

Category:Amphetamine

← Category's main topic 1

Category:Amphetamine

← Different from 1

D-methamphetamine

← Drug or therapy used for treatment 1

attention deficit hyperactivity disorder

← Has active ingredient 1

Adderall

← Kunstenpunt Knowledge Graph ID 1

Pushkin Museum of Fine Arts

← Physically interacts with 1

solute carrier family 6 member 3

Press Enter · cited answer in seconds

Summary

DL-amphetamine is a group of stereoisomers^[1]. DL-amphetamine is a type of amphetamines^[2] and 1-phenylpropan-2-amine alkaloid^[3].

References

Programmatic citations — every numbered marker resolves to a verifiable graph row below.

Direct Wikidata claims

[4] ↑ DL-amphetamine — physically interacts with (P129): Trace amine associated receptor 1. wikidata.org.
[5] ↑ DL-amphetamine — physically interacts with (P129): 5-hydroxytryptamine receptor 1A. wikidata.org.
[6] ↑ DL-amphetamine — physically interacts with (P129): solute carrier family 1 member 1. wikidata.org.
[7] ↑ DL-amphetamine — physically interacts with (P129): Solute carrier family 18 member A2. wikidata.org.
[8] ↑ DL-amphetamine — physically interacts with (P129): Flavin containing dimethylaniline monoxygenase 3. books.google.com. books.google.com. Provenance: wikidata.org.
[9] ↑ DL-amphetamine — physically interacts with (P129): cytochrome P450 family 2 subfamily D member 6. accessdata.fda.gov. accessdata.fda.gov. Provenance: wikidata.org.
[10] ↑ DL-amphetamine — physically interacts with (P129): dopamine beta-hydroxylase. books.google.com. books.google.com. Provenance: wikidata.org.
[11] ↑ DL-amphetamine — physically interacts with (P129): Solute carrier family 6 member 2. Open Targets Platform. Retrieved 2023-08-14. platform.opentargets.org. Provenance: wikidata.org.
[12] ↑ DL-amphetamine — physically interacts with (P129): solute carrier family 6 member 3. Open Targets Platform. Retrieved 2023-08-14. platform.opentargets.org. Provenance: wikidata.org.
[13] ↑ DL-amphetamine — canonical SMILES (P233): CC(CC1=CC=CC=C1)N. PubChem. Retrieved 2016-11-19. wikidata.org.
[14] ↑ DL-amphetamine — chemical formula (P274): C₉H₁₃N. PubChem. Retrieved 2016-11-19. wikidata.org.
[2] ↑ DL-amphetamine — subclass of (P279): amphetamines. wikidata.org.
[3] ↑ DL-amphetamine — subclass of (P279): 1-phenylpropan-2-amine alkaloid. wikidata.org.
[15] ↑ DL-amphetamine — part of (P361): response to amphetamine. Gene Ontology release 2019-11-16. wikidata.org.
[16] ↑ DL-amphetamine — part of (P361): cellular response to amphetamine. Gene Ontology release 2019-11-16. wikidata.org.
[17] ↑ DL-amphetamine — has use (P366): medication. wikidata.org.
[18] ↑ DL-amphetamine — found in taxon (P703): Senegalia berlandieri. Toxic amines and alkaloids from Acacia berlandieri. wikidata.org.
[19] ↑ DL-amphetamine — significant drug interaction (P769): isocarboxazid. High-priority drug–drug interactions for use in electronic health records. wikidata.org.
[20] ↑ DL-amphetamine — significant drug interaction (P769): phenelzine. High-priority drug–drug interactions for use in electronic health records. wikidata.org.
[21] ↑ DL-amphetamine — significant drug interaction (P769): procarbazine. High-priority drug–drug interactions for use in electronic health records. wikidata.org.
[22] ↑ DL-amphetamine — significant drug interaction (P769): (±)-deprenyl. High-priority drug–drug interactions for use in electronic health records. wikidata.org.
[23] ↑ DL-amphetamine — significant drug interaction (P769): tranylcypromine. High-priority drug–drug interactions for use in electronic health records. wikidata.org.
[24] ↑ DL-amphetamine — described by source (P1343): Opium Law. wikidata.org.
[25] ↑ DL-amphetamine — different from (P1889): D-methamphetamine. wikidata.org.
[26] ↑ DL-amphetamine — density (P2054): 0.936 gram per cubic metre. PubChem. pubchem.ncbi.nlm.nih.gov. Provenance: wikidata.org.
[27] ↑ DL-amphetamine — mass (P2067): 135.104799 dalton. PubChem. Retrieved 2016-10-04. wikidata.org.
[28] ↑ DL-amphetamine — melting point (P2101): 11.3 °C. chemspider.com. chemspider.com. Provenance: wikidata.org.
[29] ↑ DL-amphetamine — boiling point (P2102): 203 °C. PubChem. wikidata.org.
[30] ↑ DL-amphetamine — medical condition treated (P2175): attention deficit hyperactivity disorder. NDF-RT. Retrieved 2016-12-13. wikidata.org.
[31] ↑ DL-amphetamine — medical condition treated (P2175): narcolepsy. NDF-RT. Retrieved 2016-12-13. wikidata.org.
[32] ↑ DL-amphetamine — medical condition treated (P2175): obesity. evekeo.com. Retrieved 2017-07-30. evekeo.com. Provenance: wikidata.org.
[33] ↑ DL-amphetamine — World Health Organisation international non-proprietary name (P2275): amfetaminum. wikidata.org.
[34] ↑ DL-amphetamine — World Health Organisation international non-proprietary name (P2275): amfetamine. wikidata.org.
[35] ↑ DL-amphetamine — World Health Organisation international non-proprietary name (P2275): amfétamine. wikidata.org.
[36] ↑ DL-amphetamine — World Health Organisation international non-proprietary name (P2275): anfetamina. wikidata.org.
[37] ↑ DL-amphetamine — World Health Organisation international non-proprietary name (P2275): амфетамин. wikidata.org.
[38] ↑ DL-amphetamine — World Health Organisation international non-proprietary name (P2275): أمفيتامين. wikidata.org.
[39] ↑ DL-amphetamine — World Health Organisation international non-proprietary name (P2275): 苯丙胺. wikidata.org.

Class ancestry

[1] ↑ DL-amphetamine is an instance of group of stereoisomers (Q59199015) [P31, primary]. Wikidata. wikidata.org.

📑 Cite this page

Use these citations when quoting this entity in research, articles, AI prompts, or wherever provenance matters. We aggregate Wikidata + Wikipedia + authoritative open-data sources; the stitched, scored, cross-referenced view is what 4ort.xyz contributes.

APA

4ort.xyz Knowledge Graph. (2026). DL-amphetamine. Retrieved November 4, 2026, from https://4ort.xyz/entity/dl-amphetamine

MLA “DL-amphetamine.” 4ort.xyz Knowledge Graph, 4ort.xyz, 4 Nov. 2026, https://4ort.xyz/entity/dl-amphetamine.

BibTeX

@misc{4ortxyz_dl-amphetamine_2026, author = {{4ort.xyz Knowledge Graph}}, title = {{DL-amphetamine}}, year = {2026}, url = {https://4ort.xyz/entity/dl-amphetamine}, note = {Accessed: 2026-11-04}}

LLM prompt

According to 4ort.xyz Knowledge Graph (aggregator of Wikidata, Wikipedia, and authoritative open-data sources): DL-amphetamine — https://4ort.xyz/entity/dl-amphetamine (retrieved 2026-11-04)

Canonical URL: https://4ort.xyz/entity/dl-amphetamine · Last refreshed: November 4, 2026

Edit History

Rolling log of changes to this entity's Wikidata record. Values shown reflect the current state of each edited property — follow the history link to see the precise diff for any edit.

2d ago · ~2026-58230-13 · 2026-11-02 view diff on Wikidata ↗

P14834 → Schedule I (Russia), Schedule I (Canada), Anlage III (Germany) +3

Wikipedia languages → ['af', 'ar', 'arz', 'az', 'bg', 'bn', 'ca', 'cs', 'cy', 'da', 'de', 'el', 'en',

Sitelink count → 70

Claims rich → —

"/* wbsetdescription-set:1|ar */ مركب كيميائي منبه للجهاز العصبي"
9w ago · Carn · 2026-08-31 view diff on Wikidata ↗

P14834 → Schedule I (Russia), Schedule I (Canada), Anlage III (Germany) +3

"/* wbcreateclaim-create:1| */ P14834: Schedule I (Russia), #quickstatements; #temporary_batch_1788165634350"
24w ago · Twofivesixbot bot · 2026-05-18 view diff on Wikidata ↗

Has use → medication

Significant drug interaction → isocarboxazid, phenelzine, procarbazine +2

Density → {'unit': 'Q21604951', 'amount': '+0.936'}

Mass → {'unit': 'Q483261', 'amount': '+135.104799'}

+ 20 other properties edited (see Wikidata diff for full list)

"/* wbsetclaim-update-qualifiers:1||1|4 */ YSO ID: 5463, mv to monolingual text names on YSO statements"

Live feed via Wikidata EventStreams. New edits appear within minutes of being made on Wikidata.