2C-I
2-(4-iodo-2,5-dimethoxyphenyl)ethanamine
Overview
2C-I belongs to Psychedelics / Phenethylamines / 2C series.
Key safety note: As a potent serotonergic 2C psychedelic, 2C-I can acutely cause anxiety, confusion and perceptual overwhelm, alongside sympathomimetic and vasoconstrictive effects such as tachycardia, hypertension, mydriasis and nausea.[2]
Effects
Subjective effects vary. What a substance feels like depends on dose, individual physiology,
mindset, and setting. The points below describe commonly reported effects, not guaranteed, uniform, or
desirable outcomes.
- Strong, colourful visual effects: geometric patterning (often likened to 2C-B) and marked colour enhancement
- Stimulating, energetic body character
- Comparatively clear-headed with a balanced emotional tone at common doses
- Faster onset than some 2C compounds, with an abrupt drop-off
Dosing & duration
Harm-reduction note: These are commonly cited reference ranges, not a recommendation or a
“safe” dose. Potency, purity, body chemistry, tolerance, and drug combinations vary widely. Start
low, go slow, wait for full effects before redosing, and never assume an unknown product matches these
figures. Missing data is not evidence of safety.
Oral
Dose ranges
Oral
14–22 mg
Duration
onset
≤40 min
total
6–10 h
Chemical & Physical Properties
| Formula | C10H14INO2 |
| Molar mass | 307.13 g/mol |
| State | Solid (usually the hydrochloride salt, white microcrystalline) |
| Melting point | 246–247 °C (hydrochloride salt) |
| Boiling point | Not reported |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 1.8 (predicted, XLogP3) |
| Solubility | Not reported |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | Not reported |
| CAS (enantiomer) | |
| PubChem CID | 10267191 |
| InChIKey | PQHQBRJAAZQXHL-UHFFFAOYSA-N |
| InChI | InChI=1S/C10H14INO2/c1-13-9-6-8(11)10(14-2)5-7(9)3-4-12/h5-6H,3-4,12H2,1-2H3 |
| SMILES | COC1=CC(=C(C=C1CCN)OC)I |
Synonyms
- 2,5-dimethoxy-4-iodophenethylamine
- 4-iodo-2,5-dimethoxyphenethylamine
- 2C-I
Pharmacodynamics & Biochemistry
Serotonergic phenethylamine psychedelic acting primarily as a 5-HT2A receptor agonist. Also a potent agonist at 5-HT2C and 5-HT2B, with broad additional binding across serotonin, adrenergic and dopaminergic receptors. The iodinated member of the 2C-X halogen series and, with 2C-B, among the most explored. Noted for strong, colourful visual effects.
Biological targets
- 5-HT2A
- 5-HT2C
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| 5-HT2A receptor | Ki 3.5 ± 1.0 nM | Human |
| 5-HT2C receptor | Ki 40 ± 9.0 nM | Human |
| 5-HT1D receptor | Ki 40 nM | Human |
| 5-HT1B receptor | Ki 56 nM | Human |
| α2-adrenoceptor | Ki 70 ± 10 nM | Human |
| 5-HT1E receptor | Ki 131 nM | Human |
| α2C-adrenoceptor | Ki 315 nM | Human |
| 5-HT1A receptor | Ki 180 ± 10 nM | Human |
| α2B-adrenoceptor | Ki 608 nM | Human |
| M3 receptor | Ki 950 nM | Human |
| Serotonin transporter | Ki 4,900 ± 300 nM | Human |
| D3 receptor | Ki 5,000 ± 100 nM | Human |
| D2 receptor | Ki 2,700 ± 580 nM | Human |
| M4 receptor | Ki 1,129 nM | Human |
| 5-HT7 receptor | Ki 1,316 nM | Human |
| M2 receptor | Ki 1,429 nM | Human |
| M5 receptor | Ki 2,151 nM | Human |
| μ-opioid receptor | Ki 2,522 nM | Human |
| D4 receptor | Ki 2,788 nM | Human |
| TAAR1 | Ki 120 ± 20 nM | Rat |
| 5-HT1A receptor | EC50 4,900 ± 2,000 nM Emax 102.1% | Human |
| 5-HT2A receptor | EC50 5.9 nM Emax 70.6% | Human |
| 5-HT2B receptor | EC50 150 ± 100 nM Emax 70 ± 18% | Human |
| 5-HT2C receptor | EC50 47 ± 6.7 nM Emax 28% | Human |
| H1 receptor | Ki 6,100 ± 500 nM | Human |
| TAAR1 | EC50 2,400 ± 800 nM Emax 51 ± 21% | Mouse |
| TAAR1 | Ki 3,300 ± 100 nM | Mouse |
| TAAR1 | EC50 190 ± 110 nM Emax 50 ± 19% | Rat |
| α1A-adrenoceptor | Ki 5,100 ± 1,100 nM | Human |
Pharmacokinetics
| Bioavailability | Not reported |
| Tmax | Not reported |
| Half-life | Long |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic |
| Excretion | Not reported |
Toxicology & Safety
Harm-reduction note: Toxicity and risk depend on dose, route, purity, combinations, setting, and individual
health factors. Missing harms should never be interpreted as evidence of safety.
Not reported
As a potent serotonergic 2C psychedelic, 2C-I can acutely cause anxiety, confusion and perceptual overwhelm, alongside sympathomimetic and vasoconstrictive effects such as tachycardia, hypertension, mydriasis and nausea. Risk rises with higher doses, hot or crowded settings, adulteration, and combination with stimulants or other serotonergic drugs. 2C-I is easily confused with the far more dangerous NBOMe compounds (e.g. 25I-NBOMe), a substitution that has caused severe toxicity and deaths. Formal human toxicity data are very limited, and limited literature must never be read as evidence of safety.[2]
Legal Status
Legal note: Legal status can change over time and may vary by country, region, formulation, analogue status,
prescription context, and enforcement practice. Always confirm with current official sources before relying on this section.
US: Schedule I. UK: Class A. DE: BtMG Anlage I
Interactions & Contraindications
Drug interactions
SSRIs, SNRIs, Lithium, Tramadol, Other serotonergic drugs Can add to serotonergic load and, in principle, raise the risk of serotonin toxicity.
MAOIs May intensify and prolong effects unpredictably, warranting particular caution.
Stimulants (amphetamines, cocaine) Compound cardiovascular strain, anxiety, vasoconstriction and overheating risk.
Contraindications
Personal or family history of psychosis, schizophrenia or bipolar disorder
Cardiovascular disease, hypertension or arrhythmia significant or uncontrolled disease or hypertension.
Concurrent MAOI, SSRI/SNRI or other serotonergic medication concurrent MAO inhibitors.
Hot, dehydrating environments (overheating risk) or heavy stimulant co-use.
No interactions or contraindications listed.
Usage & Context
- Research.
Sources & Evidence
- Shulgin A, Shulgin A (1991). PiHKAL: A Chemical Love Story — entry #33 (2C-I)
- Gil-Martins E, Barbosa DJ, Borges F, et al. (2025). Toxicodynamic insights of 2C and NBOMe drugs - Is there abuse potential?. Toxicol Rep 14:101890.
PMID 39867514 · doi:10.1016/j.toxrep.2025.101890
- Rickli A, Luethi D, Reinisch J, et al. (2015). Receptor interaction profiles of novel N-2-methoxybenzyl (NBOMe) derivatives of 2,5-dimethoxy-substituted phenethylamines (2C drugs). Neuropharmacology 99:546-53.
PMID 26318099 · doi:10.1016/j.neuropharm.2015.08.034
- Simmler LD, Buchy D, Chaboz S, et al. (2016). In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1. J Pharmacol Exp Ther 357:134-44.
PMID 26791601 · doi:10.1124/jpet.115.229765
- Eshleman AJ, Forster MJ, Wolfrum KM, et al. (2014). Behavioral and neurochemical pharmacology of six psychoactive substituted phenethylamines: mouse locomotion, rat drug discrimination and in vitro receptor and transporter binding and function. Psychopharmacology (Berl) 231:875-88.
PMID 24142203 · doi:10.1007/s00213-013-3303-6
- Pottie E, Cannaert A, Stove CP (2020). In vitro structure-activity relationship determination of 30 psychedelic new psychoactive substances by means of β-arrestin 2 recruitment to the serotonin 2A receptor. Arch Toxicol 94:3449-3460.
PMID 32627074 · doi:10.1007/s00204-020-02836-w
- Elmore JS, Decker AM, de la Fuente Revenga M, et al. (2018). Comparative neuropharmacology of N-(2-methoxybenzyl)-2,5-dimethoxyphenethylamine (NBOMe) hallucinogens and their 2C counterparts in male rats. Neuropharmacology 142:54-65.
PMID 29501528 · doi:10.1016/j.neuropharm.2018.02.033
- Wikipedia: 2C-I (dosage, onset & duration) CC BY-SA 4.0