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Depressant

Trazodone

Also called Beneficat, Trazalon, Trittico

Original Wikipedia articleen.wikipedia.org/wiki/Trazodone revision used (24 October 2026)

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Part of the metabolic pathway of Trazodone. See the timeline on the metabolic highway.

Common dose · Oral50–100 mg TS

Dosage

Oral

SourceThresholdLightCommonStrongHeavy
TripSit–25–50 mg TS50–100 mg TS100–150 mg TS–

Note: Please do not take this drug unless prescribed. TS

TripSit dose text

TripSit's factsheet also states its doses as text.

Light: 25-50mg Common: 50-100mg Strong: 100-150 | Note: Please do not take this drug unless prescribed. TS

What dose are you on? (self-reported, unverified)
Read this first. These numbers come from anonymous visitors typing in a box. Nobody checks them. People misjudge, mistype, troll, or take untested products of unknown strength. They are not a dose guide and never override the sourced table above. They exist only so the sourced ranges can be compared with what people say they take. If you are deciding what to take, use the sourced table, start low, and read the risks section.
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Duration

TripSit factsheet

Onset
20-40 minutes TS
Duration
6-10 hours TS

Mixing

For best safety practice, don't mix this drug with other depressants.

Why: respiratory depression. PsychonautWiki says:

Quotes from PsychonautWiki, CC BY-SA 4.0.

Acute combinations: what happens when these are taken close together. Entries backed by a medical journal or agency are listed first.

Backed by medical journals

Awaiting sourcePeer-reviewed reports on acute combinations, from PubMed and the journals the harm reduction sites cite.

Risks and toxicity

Median lethal dose (LD50) in animals

Quoted from PubChem's Non-Human Toxicity Values, which come from the Hazardous Substances Data Bank (HSDB). PubChem describes them as: “Quantitative non-human toxicity values (e.g., lethal dose) for this compound. The data shown here are mostly for lab animals (e.g., rat, mouse, guinea pig, and rabbit).” and defines the “LD50 (median lethal dose, the estimated amount of a chemical expected to kill 50% of test animals in a single dose)”. PC

LD50 (as the source gives it)Reference
LD50 Rat oral 690 mg/kg PCLewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3502 (via HSDB record 7048)
LD50 Rat iv 91 mg/kg PCLewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3502 (via HSDB record 7048)
LD50 Rat ip 178 mg/kg PCLewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3502 (via HSDB record 7048)
LD50 Mouse oral 610 mg/kg PCLewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3502 (via HSDB record 7048)
LD50 Mouse iv 91 mg/kg PCLewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3502 (via HSDB record 7048)
Awaiting sourceToxicity, overdose signs and dependence risk from harm reduction sites and journals.

Testing

Awaiting sourceReagent reactions and test kit guidance from a harm reduction testing service.

Effects

Awaiting sourceSubjective and physical effects from PsychonautWiki or TripSit.

Overview

A novel antidepressant of the SARI class, a serotonin antagonist and reuptake inhibitor. Often used to treat depression and anxiety. It has anxiolytic and hypnotic effects. TS

Trazodone is an antidepressant medication used to treat major depressive disorder, anxiety disorders, and insomnia. It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class. The medication is taken orally.[1][2][3] WP

Common side effects include dry mouth, feeling faint, vomiting, and headache. More serious side effects may include suicidal ideation, mania, irregular heart rate, and pathologically prolonged erections. It is unclear if use during pregnancy or breastfeeding is safe. Trazodone also has sedating effects.[1][4][5] WP

Trazodone was approved for medical use in the United States in 1981. It is available as a generic medication. In 2023, it was the 21st most commonly prescribed medication in the United States and the fifth most common antidepressant, with more than 24 million prescriptions.[1][6][7] WP

History

History

Trazodone was developed in Italy, in the 1960s, by Angelini Research Laboratories as a second-generation antidepressant. It was developed according to the mental pain hypothesis, which was postulated from studying patients and which proposes that major depression is associated with a decreased pain threshold. In sharp contrast to most other antidepressants available at the time of its development, trazodone showed minimal effects on muscarinic cholinergic receptors. Trazodone was patented and marketed in many countries all over the world, starting with Italy in 1972 and West Germany in 1977. It was approved by the Food and Drug Administration (FDA) in 1981 and was the first non-tricyclic or MAOI antidepressant approved in the US.[8–13] WP

Pharmacology

Pharmacodynamics

Trazodone is a mixed agonist and antagonist of various serotonin receptors, antagonist of adrenergic receptors, weak histamine H₁ receptor antagonist, and weak serotonin reuptake inhibitor. More specifically, it is an antagonist of 5-HT2A and 5-HT2B receptors, a partial agonist of the 5-HT1A receptor, and an antagonist of the α₁- and α₂-adrenergic receptors. It is also a ligand of the 5-HT2C receptor with lower affinity than for the 5-HT2A receptor. However, it is unknown whether trazodone acts as a full agonist, partial agonist, or antagonist of the 5-HT2C receptor. Trazodone is a 5-HT1A receptor partial agonist similarly to buspirone and tandospirone but with comparatively greater intrinsic activity. A range of weak affinities (Kᵢ) have been reported for trazodone at the human histamine H₁ receptor, including 220 nM, 350 nM, 500 nM, and 1,100 nM.[19][22][33][35–39] WP

Trazodone has a minor active metabolite known as meta-chlorophenylpiperazine (mCPP), and this metabolite may contribute to some degree to the pharmacological properties of trazodone. In contrast to trazodone, mCPP is an agonist of various serotonin receptors. It has relatively low affinity for α₁-adrenergic receptors unlike trazodone, but does have high affinity for α₂-adrenergic receptors and weak affinity for the H₁ receptor. In addition to direct interactions with serotonin receptors, mCPP is a serotonin releasing agent similarly to agents like fenfluramine and MDMA. In contrast to these serotonin releasing agents however, mCPP does not appear to cause long-term serotonin depletion (a property thought to be related to serotonergic neurotoxicity).[3][35][40–44] WP

Trazodone's 5-HT2A receptor antagonism and weak serotonin reuptake inhibition form the basis of its common label as an antidepressant of the serotonin antagonist and reuptake inhibitor (SARI) type.[45] WP

Target occupancy studies

Studies have estimated occupancy of target sites by trazodone based on trazodone concentrations in blood and brain and on the affinities of trazodone for the human targets in question. Roughly half of brain 5-HT2A receptors are blocked by 1 mg of trazodone and essentially all 5-HT2A receptors are saturated at 10 mg of trazodone, but the clinically effective hypnotic doses of trazodone are in the 25–100 mg range. The occupancy of the serotonin transporter (SERT) by trazodone is estimated to be 86% at 100 mg/day and 90% at 150 mg/day. Trazodone may almost completely occupy the 5-HT2A and 5-HT2C receptors at doses of 100 to 150 mg/day. Significant occupancy of a number of other sites may also occur. However, another study estimated much lower occupancy of the SERT and 5-HT2A receptors by trazodone.[35][46–50] WP⚠ A table follows this text in the source and is not copied here. Open the source to see it.

Absorption

Trazodone is well-absorbed after oral administration. Its bioavailability is 65 to 80%. Peak blood levels of trazodone occur 1 to 2 hours after ingestion and peak levels of the metabolite mCPP occur after 2 to 4 hours. Absorption is somewhat delayed and enhanced by food.[35][40][51] WP

Distribution

Trazodone is not sequestered into any tissue. The medication is 89 to 95% protein-bound. The volume of distribution of trazodone is 0.8 to 1.5 L/kg. Trazodone is highly lipophilic.[35][40][52] WP

Metabolism

The metabolic pathways involved in the metabolism are not well-characterized. In any case, the cytochrome P450 enzymes CYP3A4, CYP2D6, and CYP1A2 may all be involved to varying extents. Trazodone is known to be extensively metabolized by the liver via hydroxylation, N-oxidation, and N-dealkylation. Several metabolites of trazodone have been identified, including a dihydrodiol metabolite (via hydroxylation), a metabolite hydroxylated at the para position of the meta-chlorophenyl ring (via CYP2D6), oxotriazolepyridinepropionic acid (TPA) and mCPP (both via N-dealkylation of the piperazinyl nitrogen mediated by CYP3A4), and a metabolite formed by N-oxidation of the piperazinyl nitrogen.[35][40][45][50][53][54] WP

CYP1A2, CYP2D6, and CYP3A4 genotypes all do not seem to predict concentrations of trazodone or mCPP. In any case, there are large interindividual variations in the metabolism of trazodone. In addition, poor metabolizers of dextromethorphan, a CYP2D6 substrate, eliminate mCPP more slowly and have higher concentrations of mCPP than extensive metabolizers.[40][45][55][56][57] WP

mCPP is formed from trazodone by CYP3A4 and is metabolized via hydroxylation by CYP2D6 (to a para-hydroxylated metabolite). It may contribute to the pharmacological actions of trazodone. mCPP levels are only 10% of those of trazodone during therapy with trazodone, but is nonetheless present at concentrations known to produce psychic and physical effects in humans when mCPP has been administered alone. In any case, the actions of trazodone, such as its serotonin antagonism, might partially overwhelm those of mCPP. As a consequence of the production of mCPP as a metabolite, patients administered trazodone may test positive on EMIT II urine tests for the presence of MDMA ("ecstasy").[35][40][50][53][58][59][60] WP

Elimination

The elimination of trazodone is biphasic: the first phase's half-life (distribution) is 3 to 6 hours, and the following phase's half-life (elimination) is 4.1 to 14.6 hours. The elimination half-life of extended-release trazodone is 9.1 to 13.2 hours. The elimination half-life of mCPP is 2.6 to 16.0 hours and is longer than that of trazodone. Metabolites are conjugated to gluconic acid or glutathione and around 70 to 75% of ¹⁴C-labelled trazodone was found to be excreted in the urine within 72 hours. The remaining drug and its metabolites are excreted in the faeces via biliary elimination. Less than 1% of the drug is excreted in its unchanged form. After an oral dose of trazodone, it was found to be excreted 20% in the urine as TPA and conjugates, 9% as the dihydrodiol metabolite, and less than 1% as unconjugated mCPP. mCPP is glucuronidated and sulfated similarly to other trazodone metabolites.[35][36][40][52][61][62][63] WP

Receptor binding · Wikipedia

Trazodone (and metabolite)

SiteTrazodonemCPP (meta-Chlorophenylpiperazine)Species
SERT (Serotonin transporter)160–>10,000202–432Human[18–21] WP
NET (Norepinephrine transporter)≥8,500≥1,940Human[19][20][21] WP
DAT (Dopamine transporter)≥7,400ND (No data)Human[19][21] WP
5-HT1A96–11844–400Human[19][22][23] WP
5-HT1B>10,00089–501Human[19][24] WP
5-HT1D106210–1,300Human[19][23][25] WP
5-HT1E>10,000ND (No data)Human[19] WP
5-HT1FND (No data)ND (No data)ND (No data)[19] WP
5-HT2A20–4532–398Human[19][26][27][28] WP
5-HT2B74–1893.2–63Human[19][26][29][30] WP
5-HT2C224–4023.4–251Human[19][26][28][31][32] WP
5-HT₃>10,000427Human[19] WP
5-HT₄ND (No data)ND (No data)ND (No data)[19] WP
5-HT5A>10,0001,354Human[19] WP
5-HT₆>10,0001,748Human[19] WP
5-HT₇1,782163Human[19] WP
α₁12–4297–2,900Human[19][20][22][23][33] WP
α1A1531,386Human[19] WP
α1BND (No data)915Human[19] WP
α1DND (No data)ND (No data)ND (No data)[19] WP
α₂106–490112–570Human[19][20][22][23][33] WP
α2A728145Human[19] WP
α2BND (No data)106Human[19] WP
α2C155124Human[19] WP
β>10,0002,500Human[19][23] WP
β₁>10,0002,359Human[19] WP
β₂>10,0003,474Human[19] WP
D₁3,7307,000Human[19][23] WP
D₂≥3,500>10,000Human[19][22][23][34] WP
D₃353>10,000Rat[19][23] WP
D₄703ND (No data)Human[19] WP
D₅>10,000>10,000Human[19][23] WP
H₁220–1,100326Human[19][22][33] WP
H₂3,290ND (No data)Human[19] WP
H₃>10,000ND (No data)Guinea pig[19] WP
H₄>10,000ND (No data)Human[19] WP
mAChRs (Muscarinic acetylcholine receptors)>10,000>10,000Human[19][22][23][34] WP
nAChRs (Nicotinic acetylcholine receptors)>10,000>10,000Human[19] WP
σ₁>10,000ND (No data)Rat[19] WP
σ₂5368,350Rat[19] WP
I₁ND (No data)759Rat[19] WP
NMDAR (N-Methyl-D-aspartate receptor) (MK-801)>10,000ND (No data)Rat[19] WP
VDCCs (Voltage-dependent calcium channels)>10,0006,043Rat[19] WP

Chemistry

Formula
C19H22ClN5O PC
CAS number
19794-93-5 PC
Molar mass (g/mol)
371.9 PC
IUPAC name (computed by PubChem)
2-[3-[4-(3-chlorophenyl)piperazin-1-yl]propyl]-[1,2,4]triazolo[4,3-a]pyridin-3-one PC
SMILES
C1CN(CCN1CCCN2C(=O)N3C=CC=CC3=N2)C4=CC(=CC=C4)Cl PC
InChIKey
PHLBKPHSAVXXEF-UHFFFAOYSA-N PC
PubChem CID
5533

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References

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  3. Other Lemke TL, Williams DA. Foye's Principles of Medicinal Chemistry. 2008
  4. Other Trazodone Use During Pregnancy
  5. Other British national formulary: BNF 69. 2015
  6. Other Top 300 of 2023
  7. Other Trazodone Drug Usage Statistics, United States, 2014 - 2023
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  52. Harm reduction site Trazodone
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