3-Hydroxyphenyl compounds

Phentolamine, sold under the brand name Regitine among others, is a non-selective α-adrenergic antagonist.

Tapentadol, sold under the brand names Nucynta and Palexia among others, is a synthetic opioid analgesic with a dual mode of action as a highly selective full agonist of the μ-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Tapentadol is used medically for the treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug.

Etilefrine, sold under the brand name Effortil among others, is a sympathomimetic medication used as an antihypotensive agent to treat orthostatic hypotension. It is usually used by mouth, but is also available as an injectable.

Edrophonium, formerly sold under the brand name Tensilon among others, is a readily reversible acetylcholinesterase inhibitor. It prevents breakdown of the neurotransmitter acetylcholine and acts by competitively inhibiting the enzyme acetylcholinesterase, mainly at the neuromuscular junction.

Ketobemidone, sold under the brand name Ketogan (a mixture of ketobemidone and Spasmolytic A29) among others, is a powerful synthetic opioid painkiller. Its effectiveness against pain is in the same range as morphine, and it also has some NMDA-antagonist properties imparted, in part, by its metabolite norketobemidone. This may make it useful for some types of pain that do not respond well to other opioids. It is marketed in Denmark, Iceland, Norway. Until 2024 it was available in, but is now withdrawn in Sweden. It is used for severe pain.

Alvimopan (trade name Entereg) is a drug which behaves as a peripherally acting μ-opioid receptor antagonist. With the limited ability to cross the blood–brain barrier and reach the μ-opioid receptors of the central nervous system, the clinically undesirable effects of centrally acting opioid antagonists (like reversal of opioid-mediated analgesia) are avoided without affecting the intended blockade of μ-opioid receptors in the gastrointestinal tract. It is currently only Food and Drug Administration approved for the treatment of postoperative ileus which it received in May 2008.

Norfenefrine, also known as '''meta-octopamine or norphenylephrine and sold under the brand name Novadral' among others, is a sympathomimetic medication which is used in the treatment of hypotension (low blood pressure). Along with its structural isomer p''-octopamine and the tyramines, norfenefrine is a naturally occurring endogenous trace amine and plays a role as a minor neurotransmitter in the brain.

Meptazinol, sold under the brand name Meptid, is an opioid analgesic developed by Wyeth in the 1970s. Indications for use in moderate to severe pain, most commonly used to treat pain in obstetrics (childbirth).

Metaraminol, also known as metaradrine and sold under the brand name Aramine among others, is a sympathomimetic medication which is used in the prevention and treatment of hypotension (low blood pressure), particularly as a complication of anesthesia. It is given by intramuscular or intravenous administration.

chemical compound

Oxantel is an anthelmintic. It has typically been used in human and animal medicine as a treatment for intestinal worms. It has also been shown to inhibit fumarate reductase in some pathogenic bacteria.

3-Hydroxybenzaldehyde is an organic compound with the formula . It is a colorless solid although most samples appear tan. Two other isomers of hydroxybenzaldehyde exist.

3-Hydroxyacetophenone is a chemical compound. It is a component of castoreum, the exudate from the castor sacs of the mature beaver.

'''meta-Tyramine, also known as m-tyramine and 3-tyramine, as well as 3-hydroxyphenethylamine', is an endogenous trace amine neuromodulator and a structural analog of phenethylamine. It is a positional isomer of para''-tyramine, and similarly to it, has effects on the adrenergic and dopaminergic systems.

Desmetramadol (), also known as '''O-desmethyltramadol (O-DSMT'''), is an opioid analgesic and the main active metabolite of tramadol. Tramadol is demethylated by the liver enzyme CYP2D6 to desmetramadol in the same way as codeine, and so similarly to the variation in effects seen with codeine, individuals who have a less active form of CYP2D6 will tend to have reduced analgesic effects from tramadol. Because desmetramadol itself does not need to be metabolized to induce an analgesic effect, it can be used in individuals with CYP2D6 inactivating mutations.

Enterolactone is an organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

3-Chlorophenol is an organic compound with the molecular formula C6H4ClOH. It is one of three isomers of monochlorophenol. It is a colorless or white solid that melts easily and exhibits significant solubility in water. Together with 3,5-dichlorophenol, it is prepared industrially by dechlorination of polychlorophenols. Alternatively, it arises via the cumene process, which starts with the alkylation of chlorobenzene with propylene.

Enterodiol is an organic compound with the formula [HOC6H4CH2CH(CH2OH)]2.

Hydroxypethidine (Bemidone) is an opioid analgesic that is an analogue of the more commonly used pethidine (meperidine). Hydroxypethidine is slightly more potent than meperidine as an analgesic, 1.5x meperidine in potency, and it also has NMDA antagonist properties like its close relative ketobemidone.

Monastrol is a cell-permeable small molecule inhibitor discovered by Thomas U. Mayer in the lab of Tim Mitchison. Monastrol was shown to inhibit the kinesin-5 (also known as KIF11, Kinesin Eg5), a motor protein important for spindle bipolarity.

Ciprefadol is an opioid analgesic that is an isoquinoline derivative most closely related to cyclazocine and picenadol, with a number of other related compounds known. Ciprefadol is a mixed agonist–antagonist at μ-opioid receptors and can partly block the effects of morphine at low doses, though at higher doses it acts more like a full agonist. It is also a potent κ-opioid agonist, unlike the corresponding N-methyl and N-phenethyl derivatives which are reasonably μ-selective agonists.

(+)-BW373U86 is an opioid analgesic drug used in scientific research.

Metacetamol (developmental code name BS-749), also known as 3-hydroxyacetanilide and AMAP, is a non-toxic regioisomer of paracetamol with analgesic and antipyretic properties, but has never been marketed as a drug.

PF-219,061 is a drug that was under development by Pfizer which acts as a potent and highly selective agonist for the dopamine D3 receptor. It was under development as a potential medication for the treatment of female sexual dysfunction. It did not advance into clinical trials.

Gepefrine, also known as 3-hydroxyamphetamine or 'α-methyl-meta-tyramine and sold under the brand names Pressionorm and Wintonin', is a sympathomimetic medication used as an antihypotensive agent which has been marketed in Germany.

Metaterol (), also known as isofenefrine, isopropylnoradrianol, and '3,β-dihydroxy-N-isopropylphenethylamine', is a sympathomimetic and bronchodilator of the phenethylamine family that was never marketed. It is structurally related to norfenefrine, phenylephrine, and etilefrine.

'''meta-Hydroxynorephedrine or 3-hydroxynorephedrine, also known as 3,β-dihydroxyamphetamine''', is an adrenergic drug of the amphetamine class which was patented as a vasopressor and nasal decongestant but was never marketed. It is the racemic form of the sympathomimetic drug metaraminol.

3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative of the arylcyclohexylamine class related to phencyclidine (PCP) that has been sold online as a designer drug.