Scaline
A scaline, also known as a substituted mescaline analogue and typically but not always a 4-substituted 3,5-dimethoxyphenethylamine, is an analogue of the phenethylamine serotonergic psychedelic mescaline.
Other related compounds include the 2C and DOx compounds as well as 3,4,5-trimethoxyamphetamine and other 4-substituted 3,5-dimethoxyamphetamines. They are also mescaline analogues, but the 2C and DOx drugs have a methoxy group at the 2 position instead of the 3 position of the phenyl ring, while TMA is an amphetamine rather than a phenethylamine.
The pharmacology of mescaline analogues has been studied. Mescaline analogues, or 4-substituted 3,5-dimethoxyphenethylamines specifically, tend to be much less potent than the 2C and DOx drugs. This relates to the fact that the 2,4,5-substitution pattern tends to be optimal in terms of receptor affinity and potency. However, mescaline analogues are frequently much more potent than mescaline.
Substituted mescaline analogues have been extensively characterized by Alexander Shulgin and described in his books such as PiHKAL and The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds as well as in his literature reviews. They have also been studied by David E. Nichols and Daniel Trachsel, among other researchers.
Use and effects
Interactions
Pharmacology
Pharmacodynamics
| Compound | 5-HT1A | 5-HT1B | 5-HT1D | 5-HT1E | 5-HT2A | 5-HT2B | 5-HT2C | 5-HT3 | 5-HT5A | 5-HT6 | 5-HT7 |
| Mescaline | – | – | 794 | – | 1,950 | 398 | – | – | – | – | – |
| Escaline | – | – | 724 | – | – | 148 | 1,950 | – | – | – | – |
| Isoproscaline | – | – | 4,790 | – | 2,750 | 263 | 2,510 | – | – | – | – |
| Cyclopropylmescaline | – | – | – | – | – | 234 | 955 | – | – | – | – |
| Allylescaline | – | – | – | 490 | 2,450 | 245 | 1,320 | – | – | – | – |
| Methallylescaline | – | – | 2,750 | – | 955 | 110 | 324 | – | – | – | – |
Society and culture
Legal status
Canada
Mescaline and 3,4,5-trimethoxyamphetamine are the only scalines that are controlled substances in Canada as of 2025.List of scalines
4-Substituted
- Allylescaline
- Amylescaline
- Benzscaline
- Biscaline
- Buscaline
- Cyclopropylmescaline
- Cycloproscaline
- 4-Desmethylmescaline
- 4-Desoxymescaline
- Difluoroescaline
- Difluoroisoproscaline
- Difluoromescaline
- Escaline
- Fluoroescaline
- Fluoromescaline
- Fluoroproscaline
- Hexylescaline
- Isobuscaline
- Isoproscaline
- Methallylescaline
- Phenescaline
- Propynylscaline
- Proscaline
- Septylescaline
- 4-Thiobuscaline
- 4-Thioescaline
- 4-Thiomescaline
- 4-Thioproscaline
- Trifluoroescaline
- Trifluoromescaline
- Trifluoroproscaline
- Viscaline
3- or 5-Extended
- Asymbescaline
- Metadifluoromescaline
- Metaescaline
- Metaproscaline
- Symbescaline
- 4-Thioasymbescaline
- 4-Thiometaescaline
- 4-Thiosymbescaline
- 4-Thiotrescaline
- Trescaline
3- or 5-Replaced
- 3-Desmethylmescaline
- 3-Thioasymbescaline
- 5-Thioasymbescaline
- 3-Thioescaline
- 3-Thiomescaline
- 3-Thiometaescaline
- 5-Thiometaescaline
- 3-Thiosymbescaline
- 3-Thiotrescaline
- 3,4,5-Trideoxymescaline
2- or 6-Substituted
- 2-Bromo-6-chloromescaline
- 2-Bromo-6-methylmescaline
- 2-Bromomescaline
- 2-Chloromescaline
- 2-Iodomescaline
- 2-Methylmescaline
- 2,6-Dibromomescaline
- 2,6-Dichloromescaline
- 2,6-Dimethylmescaline
- 2,3,4,5,6-Pentamethoxyphenethylamine
- 2,3,4,5-Tetramethoxyphenethylamine
''N''-Substituted
- N-Acetylmescaline
- N-Formylmescaline
- N,''N-Diformylmescaline
- N''-Methylmescaline
- M-NDEPA
- NBOMe-escaline
- NBOMe-mescaline
- Trichocereine
α- or β-Substituted
- BOM
- α-Ethylmescaline
- β-HOM
- 3,4,5-Trimethoxyamphetamine
Cyclized
- Bromojimscaline
- Bromotomscaline
- DEMPDHPCA-M
- Flyscaline
- Jimscaline
- Tomscaline
Other compounds
- 4-D
- 3,5-Dimethoxyphenethylamine
- Beta-D
- Isomescaline
- Lophophine
- 2-Thioisomescaline
- 3-Thioisomescaline
- 4-Thioisomescaline