Eletriptan: Difference between revisions

Eletriptan
Clinical data
Trade names	Relpax, Relert
AHFS/Drugs.com	Monograph
MedlinePlus	a603029
License data	US DailyMed: Eletriptan;
Pregnancy; category	AU: B1; ;
Routes of; administration	By mouth
ATC code	N02CC06 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	50%
Metabolism	CYP3A4
Elimination half-life	4 hours
Identifiers
	IUPAC name 3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-5-[2-(benzenesulfonyl)ethyl]-1H-indole;
CAS Number	143322-58-1 ; HBr: 177834-92-3 ;
PubChem CID	77993; HBr: 656631;
IUPHAR/BPS	40;
DrugBank	DB00216 ; HBr: DBSALT000884 ;
ChemSpider	70379 ; HBr: 570985 ;
UNII	22QOO9B8KI; HBr: M41W832TA3 ;
KEGG	D07887 ; HBr: D01973 ;
ChEBI	CHEBI:50922 ; HBr: CHEBI:61176 ;
ChEMBL	ChEMBL1510 ; HBr: ChEMBL1201003 ;
CompTox Dashboard (EPA)	DTXSID9046861 ;
ECHA InfoCard	100.167.337
Chemical and physical data
Formula	C22H26N2O2S
Molar mass	382.52 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCC[C@@H]1Cc3c[nH]c4ccc(CCS(=O)(=O)c2ccccc2)cc34;
	InChI InChI=1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-137T56T ; Key:PWVXXGRKLHYWKM-LJQANCHMSA-N ;
	(what is this?) (verify)

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Eletriptan, sold under the brand name Relpax and used in the form of eletriptan hydrobromide, is a second-generation triptan medication intended for treatment of migraine headaches.^[3]^[4] It is used as an abortive medication, blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by Pfizer Inc.

Approval and availability

Eletriptan was approved by the US Food and Drug Administration (FDA) in December 2002, for the acute treatment of migraine with or without aura in adults.^[5] It is available only by prescription in the United States and Canada. It is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. It is available in 20 mg and 40 mg strengths. But unfortunately due to unknown reasons this product is hardly available in Germany if at all.

Eletriptan was covered by U.S. Patent no. 5545644^[5]^[6] and U.S. Patent no. 6110940;^[5]^[7] both now expired.

Mechanism of action

Eletriptan is believed to reduce swelling of the blood vessels surrounding the brain. This swelling is associated with the head pain of a migraine attack. Eletriptan blocks the release of substances from nerve endings that cause more pain and other symptoms like nausea, and sensitivity to light and sound. It is thought that these actions contribute to relief of symptoms by eletriptan.

Eletriptan is a serotonin receptor agonist, specifically an agonist of certain 5-HT₁ family receptors. Eletriptan binds with high affinity to the 5-HT_[1B_, _1D_, _1F] receptors. It has a modest affinity to the 5-HT_[1A_, _1E_, _2B_, _7] receptors, and little to no affinity at the 5-HT_[2A_, _2C_, ₃_, ₄_, _5A_, _6] receptors.

Eletriptan has no significant affinity or pharmacological activity at adrenergic α₁, α₂, or β; dopaminergic D₁ or D₂; muscarinic; or opioid receptors. Eletriptan could be efficiently co-administered with nitric oxide synthase (NOS's) inhibitors for the treatment of NOS-dependent diseases (US patent US 2007/0254940).

Two theories have been proposed to explain the efficacy of 5-HT₁ receptor agonists in migraine. One theory suggests that activation of 5-HT₁ receptors located on intracranial blood vessels, including those on the arteriovenous anastomoses, leads to vasoconstriction, which is correlated with the relief of migraine headache. The other hypothesis suggests that activation of 5-HT₁ receptors on sensory nerve endings in the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.

Side effects

Common side effects include hypertension, tachycardia, headache, dizziness, drowsiness and symptoms similar to angina pectoris. Severe allergic reactions are rare.^[8]

Contraindications

Eletriptan is contraindicated in patients with various diseases of the heart and circulatory system, such as angina pectoris, severe hypertension, and heart failure, as well as in patients that have had a stroke or heart attack. This is due to the unusual side effect of coronary vasoconstriction due to serotonin 5HT_1B antagonism, which can precipitate a heart attack in those already at risk. It is also contraindicated in severe renal or hepatic impairment due to its extensive liver metabolism through CYP3A4.^[8]

Interactions

Strong inhibitors of the liver enzyme CYP3A4, such as erythromycin and ketoconazole, significantly increase blood plasma concentration of eletriptan and should be separated by at least 72 hours. Ergot alkaloids, such as dihydroergotamine, add to the drug's hypertensive effect and should be separated by at least 24 hours.^[8]

Additional chemical names

Merck Index: 3-[[(2R)-1-Methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole
5-[2-(benzenesulfonyl)ethyl]-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1H-indole
(R)-5-[2-(phenylsulfonyl)ethyl]-3-[(1-methyl-2-pyrrolidinyl)methyl]-1H-indole

Society and culture

Brand names

It is sold in the United States, Canada, Australia, and the United Kingdom under the brand name Relpax,^[2]^[9]^[1] and in several other countries under the brand name Relert.^{[citation needed]}

In the US, Relpax is marketed by Viatris after Upjohn was spun off from Pfizer.^[10]^[11]^[12]

References

^ ^a ^b "Relpax 20mg Film-Coated Tablets. - Summary of Product Characteristics (SmPC)". (emc). 3 July 2020. Retrieved 11 November 2020.
^ ^a ^b "Relpax- eletriptan hydrobromide tablet, film coated". DailyMed. 10 December 2019. Retrieved 11 November 2020.
^ Bhambri R, Mardekian J, Liu LZ, Schweizer E, Ramos E (2015). "A review of the pharmacoeconomics of eletriptan for the acute treatment of migraine". International Journal of General Medicine. 8: 27–36. doi:10.2147/IJGM.S73673. PMC 4296958. PMID 25624770.
^ Capi M, Curto M, Lionetto L, de Andrés F, Gentile G, Negro A, et al. (September 2016). "Eletriptan in the management of acute migraine: an update on the evidence for efficacy, safety, and consistent response". Therapeutic Advances in Neurological Disorders. 9 (5): 414–23. doi:10.1177/1756285616650619. PMC 4994780. PMID 27582896.
^ ^a ^b ^c "Drug Approval Package: Relpax (Eletriptan) NDA #021016". U.S. Food and Drug Administration (FDA). 4 April 2002. Retrieved 11 November 2020.
^ U.S. Patent no. 5545644, John E. Macor & Martin J. Wythes, Indole Derivatives, 13 August 1996.
^ U.S. Patent no. 6110940, Valerie Denise Harding, et al., Salts of an anti-migraine indole derivative, 29 August 2000.
^ ^a ^b ^c Jasek W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 6984–8. ISBN 978-3-85200-181-4.
^ "Relpax Product information". Health Canada. 25 April 2012. Retrieved 11 November 2020.
^ "Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan". Pfizer. 16 November 2020. Retrieved 17 June 2024 – via Business Wire.
^ "Relpax". Pfizer. Retrieved 17 June 2024.
^ "Brands". Viatris. 16 November 2020. Retrieved 17 June 2024.

[Relpax_SmPC-1] "Relpax 20mg Film-Coated Tablets. - Summary of Product Characteristics (SmPC)". (emc). 3 July 2020. Retrieved 11 November 2020.

[Relpax_FDA_label-2] "Relpax- eletriptan hydrobromide tablet, film coated". DailyMed. 10 December 2019. Retrieved 11 November 2020.

[pmid25624770-3] Bhambri R, Mardekian J, Liu LZ, Schweizer E, Ramos E (2015). "A review of the pharmacoeconomics of eletriptan for the acute treatment of migraine". International Journal of General Medicine. 8: 27–36. doi:10.2147/IJGM.S73673. PMC 4296958. PMID 25624770.

[pmid27582896-4] Capi M, Curto M, Lionetto L, de Andrés F, Gentile G, Negro A, et al. (September 2016). "Eletriptan in the management of acute migraine: an update on the evidence for efficacy, safety, and consistent response". Therapeutic Advances in Neurological Disorders. 9 (5): 414–23. doi:10.1177/1756285616650619. PMC 4994780. PMID 27582896.

[accessdata-5] "Drug Approval Package: Relpax (Eletriptan) NDA #021016". U.S. Food and Drug Administration (FDA). 4 April 2002. Retrieved 11 November 2020.

[6] U.S. Patent no. 5545644, John E. Macor & Martin J. Wythes, Indole Derivatives, 13 August 1996.

[7] U.S. Patent no. 6110940, Valerie Denise Harding, et al., Salts of an anti-migraine indole derivative, 29 August 2000.

[AC-8] Jasek W, ed. (2007). Austria-Codex (in German) (62nd ed.). Vienna: Österreichischer Apothekerverlag. pp. 6984–8. ISBN 978-3-85200-181-4.

[9] "Relpax Product information". Health Canada. 25 April 2012. Retrieved 11 November 2020.

[10] "Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan". Pfizer. 16 November 2020. Retrieved 17 June 2024 – via Business Wire.

[11] "Relpax". Pfizer. Retrieved 17 June 2024.

[12] "Brands". Viatris. 16 November 2020. Retrieved 17 June 2024.

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+{{cs1 config |name-list-style=vanc |display-authors=6}}
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-| index2_label = as salt
+| index2_label = HBr
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 | CAS_number = 143322-58-1
@@ Line 79: / Line 81: @@
 }}
-'''Eletriptan''', sold under the brand name '''Relpax''' and used in the form of eletriptan hydrobromide, is a second generation [[triptan]] [[medication]] intended for treatment of [[migraine]] [[headache]]s.<ref name="pmid25624770">{{cite journal | vauthors = Bhambri R, Mardekian J, Liu LZ, Schweizer E, Ramos E | title = A review of the pharmacoeconomics of eletriptan for the acute treatment of migraine | journal = International Journal of General Medicine | volume = 8 | issue = | pages = 27–36 | date = 2015 | pmid = 25624770 | pmc = 4296958 | doi = 10.2147/IJGM.S73673 }}</ref><ref name="pmid27582896">{{cite journal | vauthors = Capi M, Curto M, Lionetto L, de Andrés F, Gentile G, Negro A, Martelletti P | title = Eletriptan in the management of acute migraine: an update on the evidence for efficacy, safety, and consistent response | journal = Therapeutic Advances in Neurological Disorders | volume = 9 | issue = 5 | pages = 414–23 | date = September 2016 | pmid = 27582896 | pmc = 4994780 | doi = 10.1177/1756285616650619 }}</ref> It is used as an [[abortive medication]], blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by [[Pfizer|Pfizer Inc]].
+'''Eletriptan''', sold under the brand name '''Relpax''' and used in the form of eletriptan hydrobromide, is a second-generation [[triptan]] [[medication]] intended for treatment of [[migraine]] [[headache]]s.<ref name="pmid25624770">{{cite journal | vauthors = Bhambri R, Mardekian J, Liu LZ, Schweizer E, Ramos E | title = A review of the pharmacoeconomics of eletriptan for the acute treatment of migraine | journal = International Journal of General Medicine | volume = 8 | issue = | pages = 27–36 | date = 2015 | pmid = 25624770 | pmc = 4296958 | doi = 10.2147/IJGM.S73673 | doi-access = free }}</ref><ref name="pmid27582896">{{cite journal | vauthors = Capi M, Curto M, Lionetto L, de Andrés F, Gentile G, Negro A, Martelletti P | title = Eletriptan in the management of acute migraine: an update on the evidence for efficacy, safety, and consistent response | journal = Therapeutic Advances in Neurological Disorders | volume = 9 | issue = 5 | pages = 414–23 | date = September 2016 | pmid = 27582896 | pmc = 4994780 | doi = 10.1177/1756285616650619 }}</ref> It is used as an [[abortive medication]], blocking a migraine attack which is already in progress. Eletriptan is marketed and manufactured by [[Pfizer|Pfizer Inc]].
 ==Approval and availability==
-Eletriptan was approved by the US [[Food and Drug Administration]] (FDA) on December 26, 2002, for the acute treatment of migraine with or without [[Aura (symptom)|aura]] in adults.<ref name=accessdata>{{cite web | title=Drug Approval Package: Relpax (Eletriptan) NDA #021016 | website=U.S. [[Food and Drug Administration]] (FDA) | date=4 April 2002 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21016_Relpax.cfm | access-date=11 November 2020}}</ref> It is available only by [[Medical prescription|prescription]] in the United States and Canada. It is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. It is available in 20&nbsp;mg and 40&nbsp;mg strengths.
+Eletriptan was approved by the US [[Food and Drug Administration]] (FDA) in December 2002, for the acute treatment of migraine with or without [[Aura (symptom)|aura]] in adults.<ref name=accessdata>{{cite web | title=Drug Approval Package: Relpax (Eletriptan) NDA #021016 | website=U.S. [[Food and Drug Administration]] (FDA) | date=4 April 2002 | url=https://www.accessdata.fda.gov/drugsatfda_docs/nda/2002/21016_Relpax.cfm | access-date=11 November 2020}}</ref> It is available only by [[Medical prescription|prescription]] in the United States and Canada. It is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. It is available in 20&nbsp;mg and 40&nbsp;mg strengths. But unfortunately due to unknown reasons this product is hardly available in Germany if at all.
-Eletriptan was covered by {{US patent|5545644|U.S. Patent no. 5545644}}<ref name=accessdata/><ref>{{US patent|5545644|U.S. Patent  no. 5545644}}, John E. Macor &  Martin J. Wythes, ''Indole Derivatives'',  August 13, 1996.</ref> and {{US patent|6110940|U.S. Patent  no. 6110940}};<ref name=accessdata/><ref>{{US patent|6110940|U.S. Patent   no. 6110940}}, Valerie Denise Harding, ''et al.'', ''Salts of an anti-migraine indole derivative'', August 29, 2000.</ref>  both now expired.
+Eletriptan was covered by {{US patent|5545644|U.S. Patent no. 5545644}}<ref name=accessdata/><ref>{{US patent|5545644|U.S. Patent  no. 5545644}}, John E. Macor &  Martin J. Wythes, ''Indole Derivatives'', 13 August 1996.</ref> and {{US patent|6110940|U.S. Patent  no. 6110940}};<ref name=accessdata/><ref>{{US patent|6110940|U.S. Patent no. 6110940}}, Valerie Denise Harding, ''et al.'', ''Salts of an anti-migraine indole derivative'', 29 August 2000.</ref>  both now expired.
 ==Mechanism of action==
@@ Line 92: / Line 94: @@
 Eletriptan is a [[serotonin receptor agonist]], specifically an [[agonist]] of certain [[5-HT1 receptor|5-HT<sub>1</sub> family receptor]]s. Eletriptan binds with high affinity to the [[5-HT1B|5-HT<sub>[1B</sub>]]<sub>,</sub> [[5-HT1D|<sub>1D</sub>]]<sub>,</sub> [[5-HT1F|<sub>1F]</sub>]] receptors. It has a modest affinity to the [[5-HT1A|5-HT<sub>[1A</sub>]]<sub>,</sub> [[5-HT1E|<sub>1E</sub>]]<sub>,</sub> [[5-HT2B receptor|<sub>2B</sub>]]<sub>,</sub> [[5-HT7|<sub>7]</sub>]] receptors, and little to no affinity at the [[5-HT2A|5-HT<sub>[2A</sub>]]<sub>,</sub> [[5-HT2C receptor|<sub>2C</sub>]]<sub>,</sub> [[5-HT3|<sub>3</sub>]]<sub>,</sub> [[5-HT4|<sub>4</sub>]]<sub>,</sub> [[5-HT5A|<sub>5A</sub>]]<sub>,</sub> [[5-HT6|<sub>6]</sub>]] receptors.
-Eletriptan has no significant affinity or pharmacological activity at [[adrenergic receptor|adrenergic]] [[alpha-1 adrenergic receptor|α<sub>1</sub>]], [[alpha-2 adrenergic receptor|α<sub>2</sub>]], or [[beta-adrenergic receptor|β]]; [[dopamine receptor|dopaminergic]] [[D1 receptor|D<sub>1</sub>]] or [[D2 receptor|D<sub>2</sub>]]; [[muscarinic acetylcholine receptor|muscarinic]]; or [[opioid receptor]]s. Eletriptan could be efficiently co-administrated with nitric oxide synthase (NOS's) inhibitors for the treatment of NOS-dependent diseases (US patent US 2007/0254940).
+Eletriptan has no significant affinity or pharmacological activity at [[adrenergic receptor|adrenergic]] [[alpha-1 adrenergic receptor|α<sub>1</sub>]], [[alpha-2 adrenergic receptor|α<sub>2</sub>]], or [[beta-adrenergic receptor|β]]; [[dopamine receptor|dopaminergic]] [[D1 receptor|D<sub>1</sub>]] or [[D2 receptor|D<sub>2</sub>]]; [[muscarinic acetylcholine receptor|muscarinic]]; or [[opioid receptor]]s. Eletriptan could be efficiently co-administered with nitric oxide synthase (NOS's) inhibitors for the treatment of NOS-dependent diseases (US patent US 2007/0254940).
 Two theories have been proposed to explain the efficacy of 5-HT<sub>1</sub> receptor agonists in migraine. One theory suggests that activation of 5-HT<sub>1</sub> receptors located on intracranial blood vessels, including those on the arteriovenous anastomoses, leads to vasoconstriction, which is correlated with the relief of migraine headache. The other hypothesis suggests that activation of 5-HT<sub>1</sub> receptors on sensory nerve endings in the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.
@@ Line 113: / Line 115: @@
 === Brand names ===
 It is sold in the United States, Canada, Australia, and the United Kingdom under the brand name Relpax,<ref name="Relpax FDA label" /><ref>{{cite web | title=Relpax Product information | website=Health Canada | date=25 April 2012 | url=https://health-products.canada.ca/dpd-bdpp/info.do?lang=en&code=74152 | access-date=11 November 2020}}</ref><ref name="Relpax SmPC" /> and in several other countries under the brand name Relert.{{cn|date=October 2020}}
+In the US, Relpax is marketed by [[Viatris]] after Upjohn was spun off from Pfizer.<ref>{{cite web | title=Pfizer Completes Transaction to Combine Its Upjohn Business with Mylan | publisher=Pfizer | via=Business Wire | date=16 November 2020 | url=https://www.businesswire.com/news/home/20201116005378/en/ | access-date=17 June 2024}}</ref><ref>{{cite web | title=Relpax | website=Pfizer | url=https://www.pfizer.com/products/product-detail/relpax | access-date=17 June 2024}}</ref><ref>{{cite web | title=Brands | website=Viatris | date=16 November 2020 | url=https://www.viatris.com/en/products/brands | access-date=17 June 2024}}</ref>
 ==References==
 {{Reflist}}
-== External links ==
-* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/rn/143322-58-1 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Eletriptan }}
-* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/rn/177834-92-3 | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Eletriptan hydrobromide }}
 {{Serotonin receptor modulators}}
 {{Triptans}}
+{{Tryptamines}}
 {{Portal bar | Medicine}}
@@ Line 129: / Line 130: @@
 [[Category:5-HT1F agonists]]
 [[Category:Triptans]]
-[[Category:Pfizer brands]]
+[[Category:Drugs developed by Pfizer]]
 [[Category:Pyrrolidines]]
 [[Category:Benzosulfones]]
+[[Category:Tryptamines]]

v t e Tryptamines
Tryptamines	1-Methyl-T 1-Methylpsilocin 2-HO-NMT 2-Me-DET 2-Methyl-5-HT 2,N,N-TMT 4,5-DHP-DMT 4-AcO-DALT 4-AcO-DET 4-AcO-DiPT 4-AcO-DPT 4-AcO-EPT 4-AcO-MALT 4-AcO-MET 4-AcO-MiPT 4-AcO-NMT 4-AcO-TMT 4-F-5-MeO-DMT 4-Fluoro-T 4-HO-5-MeO-DMT 4-HO-DALT 4-HO-DBT 4-HO-DET 4-HO-DiPT 4-HO-DPT 4-HO-DSBT 4-HO-EPT 4-HO-MALT 4-HO-MET 4-HO-McPT 4-HO-McPeT 4-HO-MiPT 4-HO-MPT 4-HO-MsBT 4-HO-NALT 4-HO-NMT 4-HO-PiPT 4-HO-pyr-T 4-HO-TMT 4-HT 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DMT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethoxy-DMT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-MET 5-Fluoro-T 5-HO-DiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT 5-MeO-pyr-T 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine) 5-MeO-T-NBOMe 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-MT-NB3OMe 5-NOT 5,6-MeO-MiPT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-DHT 5,7-DHT 6-Fluoro-DMT 6-Fluoro-T 6-MeO-DMT 6-MeO-T 6-Methyl-T 7-Chloro-T 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Aeruginascin (4-PO-TMT) AGH-107 AGH-192 AH-494 ALiPT Alpertine Baeocystin (4-PO-NMT) Benzotript (4-chlorobenzoyl-L-tryptophan) Bufotenidine (5-HTQ) Bufotenin (5-HO-DMT) Convolutindole A CP-132,484 DALT DBT Desformylflustrabromine DET DiPT DMT DPT E-6801 E-6837 EiPT EMDT EPT Ethocybin (4-PO-DET) FGIN-127 FGIN-143 FT-104 HIOC Idalopirdine Indolylethylfentanyl Indorenate Iprocin (4-HO-DiPT) Isamide Lespedamine MBT MET Milipertine Miprocin (4-HO-MiPT) MiPT MPT MS-245 MSBT N-Feruloylserotonin (moschamine) NET/NETP NiPT NMT Norbaeocystin (4-PO-T) NTBT O-4310 O-Pivalylbufotenine Oxypertine PiPT Psilacetin (O-acetylpsilocin; 4-AcO-DMT) Psilocin (4-HO-DMT) Psilocybin (4-PO-DMT) Pyr-T RS134-49 Serotonin (5-HT) Solypertine ST-1936 Tryptamine (T) Tryptophan Yuremamine Z2876442907
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301
α-Alkyltryptamines	2,α-DMT 4-HO-αMT 4-HO-MPMI (lucigenol) 4-Me-αET 4-Me-αMT 5-Chloro-αET 5-Chloro-αMT 5-Ethoxy-αMT 5-Fluoro-αET 5-Fluoro-αMT 5-iPrO-αMT 5-MeO-α,N,N-TMT 5-MeO-αET 5-MeO-αMT 5-MeO-MPMI 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Methyl-αET α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT) α-Methyltryptophan (αMTP) α,N-DMT (N-methyl-αMT) α,N,N-TMT α,N,O-TMS αET (etryptamine) αMT AL-37350A (4,5-DHP-αMT) BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT BNC-210 BW-723C86 CP-135807 IPAP (α,N-DPT) MPMI
Triptans	Almotriptan Donitriptan Eletriptan Frovatriptan L-694247 Rizatriptan Sumatriptan Zolmitriptan
Cyclized tryptamines	Bay R 1531 Ciclindole Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD) Flucindole Harmala alkaloids and β-carbolines (e.g., 6-MeO-THH, 9-Me-BC, β-carboline (norharman), harmaline, harmalol, harmane, harmine, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids and related (e.g., DM-506 (ibogaminalog), ibogaine, ibogamine, noribogaine, tabernanthalog, tabernanthine) LY-266,097 Metralindole NDTDI PHA-57378 PNU-22394 PNU-181731 RU-28306 Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine)
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT AAZ-A-154 (DLX-001) isoAMT isoDMT Isotryptamine (isoT) PNU-181731 Ro60-0175
Related compounds	2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT AAZ-A-154 AL-34662 AL-38022A Benzofurans (e.g., 3-APB, 5-MeO-DiBF, BPAP, dimemebfe, mebfap) BRL-54443 CP-94253 EMD-386088 I-32 IAL Latrepirdine LY-367265 Non-tryptamine triptans (e.g., avitriptan, LY-334370, naratriptan) Pirlindole (R)-69 (3IQ) Ro60-0213 RU-24,969 Sertindole SN-22 Tepirindole Tetrindole VER-3323 VU6067416 YM-348