word-forming element meaning "in; into," from French and Old French en-, from Latin in- "in, into" (from PIE root *en "in"). Typically assimilated before -p-, -b-, -m-, -l-, and -r-. Latin in- became en- in French, Spanish, Portuguese, but remained in- in Italian.

Also used with native and imported elements to form verbs from nouns and adjectives, with a sense "put in or on" (encircle), also "cause to be, make into" (endear), and used as an intensive (enclose). Spelling variants in French that were brought over into Middle English account for parallels such as ensure/insure, and most en- words in English had at one time or another a variant in in-, and vice versa.

word-forming element meaning "make, make into," from French -fier, from Latin -ficare, combining form of facere "to make" (from PIE root *dhe- "to set, put").

word-forming element meaning "long, abnormally large, on a large scale," taken into English via French and Medieval Latin from Greek makros "long, large," from PIE root *mak- "long, thin."

word-forming element meaning "under, beneath; less, less than" (in chemistry, indicating a lesser oxidation), from Greek hypo (prep. and adverb) "under, beneath; up from under; toward and under (i.e. into)," from PIE root *upo "under."

word-forming element meaning "across, beyond, through, on the other side of, to go beyond," from Latin trans (prep.) "across, over, beyond," perhaps originally present participle of a verb *trare-, meaning "to cross," from PIE *tra-, variant of root *tere- (2) "cross over, pass through, overcome." In chemical use indicating "a compound in which two characteristic groups are situated on opposite sides of an axis of a molecule" [Flood].

variant of in- before -b-, -m-, -p- in the sense of "not, opposite of" (immobile, impersonal; see in- (2)) as well as "in, into" (implant, impoverish; see in- (1)). In some English words it alternates with em- (1).

word-forming element meaning "put in or into, bring to a certain state," sometimes intensive, from French assimilation of en- "in, into" (see en- (1)) to following labial stop (-b-, -p-, and often -m-), or from the same development in later Latin in- (to im-). "This rule was not fully established in spelling before the 17th c." [OED], but it is likely the pronunciation shift was in Old French and Middle English and spelling was slow to conform. Also a living prefix in English used to form verbs from adjectives and nouns (embitter, embody). In words such as emancipate, emerge, emit, emotion the e- is a reduced form of Latin ex- (see ex-) before -m-.

word-forming element meaning "against, in opposition," from Latin adverb and preposition contra "against" (see contra (prep., adv.)). The Latin word was used as a prefix in Late Latin. In French, it became contre- and passed into English as counter-. The Old English equivalent was wiðer (surviving in withers and widdershins), from wið "with, against."

word-forming element meaning "within, inside, on the inside," from Latin preposition intra "on the inside, within, in, into;" of time, "during, in the course of," related to inter "between," from PIE *en-t(e)ro-, from root *en "in." Commonly opposed to extra-, and compare inter-. The use of intra as a prefix was rare in classical Latin.

element meaning "into, in, on, upon" (also im-, il-, ir- by assimilation of -n- with following consonant), from Latin in- "in," from PIE root *en "in."

In Old French (and hence in Middle English) this often became en-, which in English had a strong tendency to revert to Latin in-, but not always, which accounts for pairs such as enquire/inquire. There was a native form, which in West Saxon usually appeared as on- (as in Old English onliehtan "to enlighten"), and some of those verbs survived into Middle English (such as inwrite "to inscribe"), but all now seem to be extinct.

Not related to in- (1) "not," which also was a common prefix in Latin, causing confusion: to the Romans impressus could mean "pressed" or "unpressed;" inaudire meant "to hear," but inauditus meant "unheard of;" in Late Latin investigabilis could mean "that may be searched into" or "that cannot be searched into." Latin invocatus was "uncalled, uninvited," but invocare was "to call, appeal to."

The trouble has continued in English; the hesitation over what is meant by inflammable being a commonly cited example. Implume (1610s) meant "to feather," but implumed (c. 1600) meant "unfeathered." Impliable can mean "capable of being implied" (1865) or "inflexible" (1734). Impartible in 17c. could mean "incapable of being divided" or "capable of being imparted." Impassionate can be "free from passion" or it can mean "strongly stirred by passion." Inanimate (adj.) is "lifeless," but Donne uses inanimate (v.) to mean "infuse with life or vigor." Irruption is "a breaking in," but irruptible is "unbreakable."

In addition to improve "use to one's profit," Middle English also had a verb improve meaning "to disprove" (15c.). To inculpate is "to accuse," but inculpable means "not culpable, free from blame." Infestive has meant "troublesome, annoying" (1560s, from infest) and "not festive" (1620s). In Middle English inflexible could mean "incapable of being bent" or "capable of being swayed or moved." In 17c., informed could mean "current in information," formed, animated," or "unformed, formless" ("This was an awkward use" [OED]). Inhabited has meant "dwelt in" (1560s) and "uninhabited" (1610s); inhabitable likewise has been used on opposite senses, a confusion that goes back to Late Latin.